Octet / Reactions

Sharpless Asymmetric Epoxidation

Included in Reactions.

Addition

Source Details

Id

sharpless-epoxidation

Name
{
  "en": "Sharpless Asymmetric Epoxidation",
  "ar": "Sharpless Asymmetric الإبوكسدة",
  "cs": "Sharpless Asymetricky Epoxidace",
  "da": "Sharpless Asymmetric Epoxidering",
  "de": "Sharpless Asymmetric Epoxidierung",
  "el": "Ασύμμετρη εποξείδωση Sharpλιγότερο",
  "es-419": "Sharpless Asymmetric Epoxidación",
  "es-ES": "Sharpless Asymmetric Epoxidación",
  "es": "Sharpless Asymmetric Epoxidación",
  "fi": "Sharpless Asymmetric Epoksidointi",
  "fr": "Sharpless Asymmetric Époxydation",
  "he": "Sharpless Asymmetric אפוקסידציה",
  "hr": "Sharpless Asimetricno Epoksidacija",
  "hu": "Sharpkevesebb mintzimmetrikus epoxidáció",
  "id": "Epoksidasi Asimetris Sharpless",
  "it": "Sharpless Asymmetric Epossidazione",
  "ja": "Sharpless不斉エポキシ化",
  "ko": "Sharpless 비대칭 에폭시화",
  "lv": "Sharpless Asimetrisks Epoksidesana",
  "nb": "Sharpless Asymmetric Epoksidering",
  "nl": "Sharpless Asymmetric Epoxidatie",
  "pl": "Sharpless Asymetryczny Epoksydacja",
  "pt-BR": "Sharpless Asymmetric Epoxidação",
  "pt-PT": "Sharpless Asymmetric Epoxidação",
  "ro": "Sharpless Asymmetric Epoxidare",
  "ru": "Sharpless Асимметричный Эпоксидирование",
  "sk": "Sharpless Asymetricky Epoxidacia",
  "sl": "Sharpless Asimetricno Epoksidacija",
  "sv": "Sharpless Asymmetric Epoxidering",
  "th": "อีพอกซิเดชันแบบไม่สมมาตรของ Sharpless",
  "tr": "Sharpdaha az olarakimetrik epoksidolarakyüzerindeu",
  "uk": "Sharpless Асиметричний Епоксидування",
  "vi": "Epoxy hóa bất đối Sharpless",
  "zh-Hans": "Sharpless 不对称环氧化",
  "zh": "Sharpless 不对称环氧化"
}
Type
{
  "en": "Addition",
  "ar": "إضافة",
  "cs": "Adice",
  "da": "Addition",
  "de": "Addition",
  "el": "Προσθήκη",
  "es-419": "Adición",
  "es-ES": "Adición",
  "es": "Adición",
  "fi": "Additio",
  "fr": "Addition",
  "he": "סיפוח",
  "hr": "Adicija",
  "hu": "Addíció",
  "id": "Adisi",
  "it": "Addizione",
  "ja": "付加",
  "ko": "첨가",
  "lv": "Pievienošana",
  "nb": "Addisjon",
  "nl": "Additie",
  "pl": "Addycja",
  "pt-BR": "Adição",
  "pt-PT": "Adição",
  "ro": "Adiție",
  "ru": "Присоединение",
  "sk": "Adícia",
  "sl": "Adicija",
  "sv": "Addition",
  "th": "การเติม",
  "tr": "Katılma",
  "uk": "Приєднання",
  "vi": "Cộng",
  "zh-Hans": "加成",
  "zh": "加成"
}
Starting Material

C/C=C/CO

Product

CC1OC1CO

Reagents

TBHP (t-BuOOH), Ti(OiPr)₄, Tartrate ester (D or L)

Mechanism
[
  {
    "smiles": "C/C=C/CO",
    "description": {
      "en": "Allylic alcohol (must have OH)",
      "ar": "أليلي كحول (يجب have OH)",
      "cs": "Allylic alkohol (musi have OH)",
      "da": "Allylic alkohol (must have OH)",
      "de": "Allylic Alkohol (must have OH)",
      "el": "Allylic αλκοόλη (must have OH)",
      "es-419": "Alcohol alílico (debe tener OH)",
      "es-ES": "Alcohol alílico (debe tener OH)",
      "es": "Alcohol alílico (debe tener OH)",
      "fi": "Allylic alkoholi (must have OH)",
      "fr": "Allylic alcool (must have OH)",
      "he": "אלילי אלכוהול (חייב have OH)",
      "hr": "Allylic alkohol (mora have OH)",
      "hu": "Allylic alkohol (must have OH)",
      "id": "Alkohol alilik (harus memiliki OH)",
      "it": "Allylic alcol (must have OH)",
      "ja": "アリルアルコール(OHが必要)",
      "ko": "알릴 알코올(OH가 있어야 함)",
      "lv": "Allylic spirts (jabut have OH)",
      "nb": "Allylic alkohol (must have OH)",
      "nl": "Allylisch alcohol (must have OH)",
      "pl": "Allylic alkohol (musi have OH)",
      "pt-BR": "Allylic álcool (must have OH)",
      "pt-PT": "Allylic álcool (must have OH)",
      "ro": "Allylic alcool (must have OH)",
      "ru": "Allylic спирт (должен have OH)",
      "sk": "Allylic alkohol (musi have OH)",
      "sl": "Allylic alkohol (mora have OH)",
      "sv": "Allylic alkohol (must have OH)",
      "th": "แอลกอฮอล์แอลลิลิก (ต้องมี OH)",
      "tr": "Allylic alkol (must have OH)",
      "uk": "Allylic спирт (має have OH)",
      "vi": "Ancol allylic (phải có OH)",
      "zh-Hans": "烯丙醇(必须有 OH)",
      "zh": "烯丙醇(必须有 OH)"
    }
  },
  {
    "smiles": "CC1OC1CO",
    "description": {
      "en": "Enantiomerically enriched epoxide",
      "ar": "Enantiomerically enriched إبوكسيد",
      "cs": "Enantiomerně obohacený epoxid",
      "da": "Enantiomerically enriched epoxid",
      "de": "Enantiomerically enriched Epoxid",
      "el": "Enantiomerically enriched epoxide",
      "es-419": "Enantiomerically enriched epóxido",
      "es-ES": "Enantiomerically enriched epóxido",
      "es": "Enantiomerically enriched epóxido",
      "fi": "Enantiomerically enriched epoksidi",
      "fr": "Enantiomerically enriched époxyde",
      "he": "Enantiomerically enriched אפוקסיד",
      "hr": "Enantiomerno obogaćeni epoksid",
      "hu": "Enantiomerically enriched epoxide",
      "id": "Epoksida diperkaya enansiomer",
      "it": "Enantiomerically enriched epossido",
      "ja": "エナンチオマー過剰のエポキシド",
      "ko": "거울상 이성질체가 풍부한 에폭사이드",
      "lv": "Enantiomēriski bagātināts epoksīds",
      "nb": "Enantiomerically enriched epoksid",
      "nl": "Enantiomeer verrijkt epoxide",
      "pl": "Epoksyd wzbogacony enancjomerycznie",
      "pt-BR": "Enantiomerically enriched epóxido",
      "pt-PT": "Enantiomerically enriched epóxido",
      "ro": "Enantiomerically enriched epoxid",
      "ru": "Энантиомерно обогащенный эпоксид",
      "sk": "Enantiomérne obohatený epoxid",
      "sl": "Enantiomerno obogaten epoksid",
      "sv": "Enantiomerically enriched epoxid",
      "th": "อีพอกไซด์ที่อุดมด้วยเอนันติโอเมอร์หนึ่ง",
      "tr": "Enantiomerically enriched epoxide",
      "uk": "Енантіомерно збагачений епоксид",
      "vi": "Epoxit giàu đối quang",
      "zh-Hans": "对映体富集的环氧化物",
      "zh": "对映体富集的环氧化物"
    }
  }
]
Stereochemistry
{
  "en": "Enantioselective: D-(-)-tartrate or L-(+)-tartrate controls face of attack",
  "ar": "Enantioselective: D-(-)-tartrate أو L-(+)-tartrate controls وجه من هجوم",
  "cs": "Enantioselective: D-(-)-tartrate nebo L-(+)-tartrate controls face z utok",
  "da": "Enantioselective: D-(-)-tartrate eller L-(+)-tartrate controls face of attack",
  "de": "Enantioselective: D-(-)-tartrate oder L-(+)-tartrate controls face of attack",
  "el": "Enantioselective: D-(-)-tartrσεe ή L-(+)-tartrσεe cσεtrols face της επίθεση",
  "es-419": "Enantioselective: D-(-)-tartrate o L-(+)-tartrate controls cara of attack",
  "es-ES": "Enantioselective: D-(-)-tartrate o L-(+)-tartrate controls cara of attack",
  "es": "Enantioselective: D-(-)-tartrate o L-(+)-tartrate controls cara of attack",
  "fi": "Enantioselective: D-(-)-tartrate tai L-(+)-tartrate controls face of attack",
  "fr": "Enantioselective: D-(-)-tartrate ou L-(+)-tartrate controls face of attack",
  "he": "Enantioselective: D-(-)-tartrate או L-(+)-tartrate controls פנים של תקיפה",
  "hr": "Enantioselective: D-(-)-tartrate ili L-(+)-tartrate controls face od napad",
  "hu": "Enantioselective: D-(-)-tartrnále vagy L-(+)-tartrnále controls face of támadás",
  "id": "Enantioselektif: D-(-)-tartrat atau L-(+)-tartrat mengontrol sisi serangan",
  "it": "Enantioselective: D-(-)-tartrate o L-(+)-tartrate controls faccia of attack",
  "ja": "エナンチオ選択的: D-(-)-tartrateまたはL-(+)-tartrateが攻撃面を制御する",
  "ko": "거울상선택적: D-(-)-타르트레이트 또는 L-(+)-타르트레이트가 공격 면을 제어함",
  "lv": "Enantioselective: D-(-)-tartrate vai L-(+)-tartrate controls face nav uzbrukums",
  "nb": "Enantioselective: D-(-)-tartrate eller L-(+)-tartrate controls face of attack",
  "nl": "Enantioselective: D-(-)-tartrate of L-(+)-tartrate controls face of attack",
  "pl": "Enantioselective: D-(-)-tartrate lub L-(+)-tartrate controls face z atak",
  "pt-BR": "Enantioselective: D-(-)-tartrate ou L-(+)-tartrate controls face of attack",
  "pt-PT": "Enantioselective: D-(-)-tartrate ou L-(+)-tartrate controls face of attack",
  "ro": "Enantioselective: D-(-)-tartrate sau L-(+)-tartrate controls față of attack",
  "ru": "Enantioselective: D-(-)-tartrate или L-(+)-tartrate controls face из атака",
  "sk": "Enantioselective: D-(-)-tartrate alebo L-(+)-tartrate controls face z utok",
  "sl": "Enantioselective: D-(-)-tartrate ali L-(+)-tartrate controls face od napad",
  "sv": "Enantioselective: D-(-)-tartrate eller L-(+)-tartrate controls face of attack",
  "th": "เลือกจำเพาะต่อเอนันติโอเมอร์: D-(-)-ทาร์เทรต หรือ L-(+)-ทาร์เทรต ควบคุมด้านที่ถูกโจมตี",
  "tr": "Enantioselective: D-(-)-tartrdee veya L-(+)-tartrdee cüzerindetrols face saldırı",
  "uk": "Enantioselective: D-(-)-tartrate або L-(+)-tartrate controls face з атака",
  "vi": "Chọn lọc đối quang: D-(-)-tartrate hoặc L-(+)-tartrate kiểm soát mặt tấn công",
  "zh-Hans": "对映选择性:D-(-)-酒石酸酯或 L-(+)-酒石酸酯控制进攻面",
  "zh": "对映选择性:D-(-)-酒石酸酯或 L-(+)-酒石酸酯控制进攻面"
}
Tips
[
  {
    "en": "Requires allylic alcohol (OH directs reaction)",
    "ar": "Requires أليلي كحول (OH directs تفاعل)",
    "cs": "Requires allylic alkohol (OH directs reakce)",
    "da": "Requires allylic alkohol (OH directs reaction)",
    "de": "Requires allylic Alkohol (OH directs reaction)",
    "el": "Requires allylic αλκοόλη (OH directs αντίδραση)",
    "es-419": "Requiere alcohol alílico (OH dirige la reacción)",
    "es-ES": "Requiere alcohol alílico (OH dirige la reacción)",
    "es": "Requiere alcohol alílico (OH dirige la reacción)",
    "fi": "Requires allylic alkoholi (OH directs reaction)",
    "fr": "Requires allylic alcool (OH directs reaction)",
    "he": "Requires אלילי אלכוהול (OH directs תגובה)",
    "hr": "Requires allylic alkohol (OH directs reakcija)",
    "hu": "Requires allylic alkohol (OH directs reakció)",
    "id": "Memerlukan alkohol alilik (OH mengarahkan reaksi)",
    "it": "Requires allylic alcol (OH directs reaction)",
    "ja": "アリルアルコールが必要(OHが反応を配向する)",
    "ko": "알릴 알코올이 필요함(OH가 반응을 지향함)",
    "lv": "Requires allylic spirts (OH directs reakcija)",
    "nb": "Requires allylic alkohol (OH directs reaction)",
    "nl": "Vereist allylisch alcohol (OH stuurt de reactie)",
    "pl": "Requires allylic alkohol (OH directs reakcja)",
    "pt-BR": "Requires allylic álcool (OH directs reaction)",
    "pt-PT": "Requires allylic álcool (OH directs reaction)",
    "ro": "Requires allylic alcool (OH directs reaction)",
    "ru": "Requires allylic спирт (OH directs реакция)",
    "sk": "Requires allylic alkohol (OH directs reakcia)",
    "sl": "Requires allylic alkohol (OH directs reakcija)",
    "sv": "Requires allylic alkohol (OH directs reaction)",
    "th": "ต้องใช้แอลกอฮอล์แอลลิลิก (OH ชี้นำปฏิกิริยา)",
    "tr": "Requires allylic alkol (OH directs reaksiyüzerinde)",
    "uk": "Requires allylic спирт (OH directs реакція)",
    "vi": "Cần ancol allylic (OH định hướng phản ứng)",
    "zh-Hans": "需要烯丙醇(OH 导向反应)",
    "zh": "需要烯丙醇(OH 导向反应)"
  },
  {
    "en": "D-tartrate → attacks from \"front\" (mnemonic)",
    "ar": "D-tartrate → يهاجم من \"front\" (mnemonic)",
    "cs": "D-tartrate → utoci z \"front\" (mnemonic)",
    "da": "D-tartrate → angriber fra \"front\" (mnemonic)",
    "de": "D-tartrate → greift an aus \"front\" (mnemonic)",
    "el": "D-tartrσεe → επιτίθεται από \"frσεt\" (mnemσεic)",
    "es-419": "D-tartrate → ataca desde \"front\" (mnemonic)",
    "es-ES": "D-tartrate → ataca desde \"front\" (mnemonic)",
    "es": "D-tartrate → ataca desde \"front\" (mnemonic)",
    "fi": "D-tartrate → hyökkää lähtien \"front\" (mnemonic)",
    "fr": "D-tartrate → attaque à partir de \"front\" (mnemonic)",
    "he": "D-tartrate → תוקף מ \"front\" (mnemonic)",
    "hr": "D-tartrate → napada iz \"front\" (mnemonic)",
    "hu": "D-tartrnále → támad ebből \"front\" (mnemonic)",
    "id": "D-tartrat → menyerang dari \"depan\" (mnemonik)",
    "it": "D-tartrate → attacca da \"front\" (mnemonic)",
    "ja": "D-tartrate → 前面から攻撃(覚え方)",
    "ko": "D-타르트레이트 → \"앞쪽\"에서 공격(암기법)",
    "lv": "D-tartrate → uzbruk nav \"front\" (mnemonic)",
    "nb": "D-tartrate → angriper fra \"front\" (mnemonic)",
    "nl": "D-tartrate → valt aan uit \"front\" (mnemonic)",
    "pl": "D-tartrate → atakuje z \"front\" (mnemonic)",
    "pt-BR": "D-tartrate → ataca de \"front\" (mnemonic)",
    "pt-PT": "D-tartrate → ataca de \"front\" (mnemonic)",
    "ro": "D-tartrate → atacă din \"front\" (mnemonic)",
    "ru": "D-tartrate → атакует из \"front\" (mnemonic)",
    "sk": "D-tartrate → utoci z \"front\" (mnemonic)",
    "sl": "D-tartrate → napade iz \"front\" (mnemonic)",
    "sv": "D-tartrate → attackerar från \"front\" (mnemonic)",
    "th": "D-ทาร์เทรต → โจมตีจาก \"ด้านหน้า\" (ตัวช่วยจำ)",
    "tr": "D-tartrdee → saldırır den \"früzerindet\" (mnemüzerindeic)",
    "uk": "D-tartrate → атакує з \"front\" (mnemonic)",
    "vi": "D-tartrate → tấn công từ \"mặt trước\" (mẹo nhớ)",
    "zh-Hans": "D-酒石酸酯 → 从“前面”进攻(记忆法)",
    "zh": "D-酒石酸酯 → 从“前面”...
Related Reactions

epoxidation

Is Free

false