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By Frederick Winthrop Faxon

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R R m-CPBA NHCBZ R = NHCBZ = CH2OH = CH2OAc = CO2Me = CH2NHCBZ = CH2OTBDMS CH2Cl2, 25 °C R + O O NHCBZ 86% 83% 72% 59% 81% 54% NHCBZ 100 100 100 100 100 0 0 0 0 0 0 100 Presence of H-bonding, directing substituent enhances rate and yield of reaction. O Witiak J. Med. Chem. 1989, 32, 214. Rotella Tetrahedron Lett. 1989, 30, 1913. O O i X Pr i m-CPBA X O 80% n = 1, X = NH X=O n = 2, X = NH X=O X Pr + CH2Cl2, 25 °C n i Pr O n 20 3 20 3 n 1 1 1 1 Mohamadi Tetrahedron Lett. 1989, 30, 1309. OH O OH O O H2O2 / NaOH / MeOH / 0 °C Ti(iPrO)4 / tBuOOH / CH2Cl2 / –15 °C OH O + O 40 : 60 >99 : 1 Ollis Tetrahedron Lett.

Soc. 1966, 88, 3334. 24 Reaction Mechanisms and Conformational Effects on Reactivity Dale L. Boger B. Alcohol Oxidations R H R' OH O fast R + HO Cr OH H R' O O slow O Cr O R O OH + R' OH Cr O OH ( CrO3 + H2O ) Westheimer J. Am. Chem. Soc. 1951, 73, 65. O fast OH tBu Cr O t Bu O O slow tBu OH ktrans O O H OH fast tBu H t Bu Cr OH O O slow H tBu kcis kcis The rate determining step for the alcohol oxidation is break down of the chromate ester with cleavage of C–H bond and O–Cr bond. = 4 ktrans Destabilizing 1,3-diaxial interactions in cis chromate ester accelerate its breakdown to the ketone (would be slower if the slow step for the reaction were formation of chromate ester).

The epoxide C–O bonds are formed simultaneously. Steric factors: 1. Bulky hydroperoxide is forced to adopt a single orientation when bound in a bidentate fashion. 2. The allylic alkoxide is thereby restricted to reaction at a single coordination site on the metal center. Steric interactions of the bound substrate with the catalyst framework provide for the kinetic resolution patterns. 3. Efficient catalytic turnover provided by the labile coordinated ester, permitting rapid alkoxide–alcohol exchange.

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A Bibliography of the Modern Chap-Books and their Imitators by Frederick Winthrop Faxon

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