ChemInform Abstract: Chiral Synthesis via Organoboranes. Part 35. Simple Procedures for the Efficient Recycling of the Terpenyl Chiral Auxiliaries and Convenient Isolation of the Homoallylic Alcohols in Asymmetric Allyl- and Crotylboration of Aldehydes.

H. C. BROWN,

H. C. BROWN

H. C. Brown a. R. B. Wetherill Lab. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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U. S. RACHERLA,

U. S. RACHERLA

H. C. Brown a. R. B. Wetherill Lab. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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Y. LIAO,

Y. LIAO

H. C. Brown a. R. B. Wetherill Lab. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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V. V. KHANNA,

V. V. KHANNA

H. C. Brown a. R. B. Wetherill Lab. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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H. C. BROWN,

H. C. BROWN

H. C. Brown a. R. B. Wetherill Lab. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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U. S. RACHERLA,

U. S. RACHERLA

H. C. Brown a. R. B. Wetherill Lab. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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Y. LIAO,

Y. LIAO

H. C. Brown a. R. B. Wetherill Lab. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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V. V. KHANNA,

V. V. KHANNA

H. C. Brown a. R. B. Wetherill Lab. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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First published: April 6, 1993

https://doi.org/10.1002/chin.199314054

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Abstract

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ChemInform Abstract

The usual work-up of the products, e.g. (I), of asymmetric allyl or crotyl borination with alkaline hydrogen peroxide proves to be disadvantageous as the chiral auxiliary is destroyed during the oxidation step. Therefore, the authors investigated several work-up procedures which recover the chiral auxiliary, e.g. α-pinene ( III).