Octet

Octet / Reactions

Sharpless Asymmetric Epoxidation

Sharpless Asymmetric Epoxidation (Addition.) Converts C/C=C/CO to CC1OC1CO using TBHP (t-BuOOH), Ti(OiPr)₄, Tartrate ester (D or L). Stereochemistry: Enantioselective: D-(-)-tartrate or L-(+)-tartrate controls face of attack.

Addition

Reaction details

Name

Sharpless Asymmetric Epoxidation

Type

Addition

Starting Material

C/C=C/CO

Product

CC1OC1CO

Reagents

  • TBHP (t-BuOOH)

  • Ti(OiPr)₄

  • Tartrate ester (D or L)

Mechanism
  1. Smiles

    C/C=C/CO

    Description

    Allylic alcohol (must have OH)

  2. Smiles

    CC1OC1CO

    Description

    Enantiomerically enriched epoxide

Stereochemistry

Enantioselective: D-(-)-tartrate or L-(+)-tartrate controls face of attack

Tips

  1. Requires allylic alcohol (OH directs reaction)

  2. D-tartrate → attacks from "front" (mnemonic)

  3. L-tartrate → attacks from "back"

  4. Nobel Prize 2001 (Sharpless)

Related Reactions

  • epoxidation

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Reactions

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Source collection

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Substitution

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SN2 with Cyanide (SN2 Substitution.) Converts CCI to CC#N using NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration.

Substitution

SN1 Solvolysis

SN1 Solvolysis (SN1 Substitution.) Converts CC(C)(C)Br to CC(C)(C)O using H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral ce...

Substitution

SN2 with Tosylate Leaving Group

SN2 with Tosylate Leaving Group (SN2 Substitution.) Converts CCOS(=O)(=O)c1ccc(C)cc1 to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

SN2 with Azide

SN2 with Azide (SN2 Substitution.) Converts CCBr to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

E2 Elimination

E2 Elimination (E2 Elimination.) Converts CC(Br)CC to CC=CC using KOtBu, NaOEt, NaOH (conc.). Conditions: Strong base, heat in t-BuOH or EtOH. Stereochemistry: Anti-periplanar geometry required. E/Z depends on which H is removed..

Elimination

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