Chiral synthesis via organoboranes. 18. Selective reductions. 43. Diisopinocampheylchloroborane as an excellent chiral reducing reagent for the synthesis of halo …

M Srebnik, PV Ramachandran…

文献索引：Srebnik, Morris; Ramachandran, P.V.; Brown, Herbert C. Journal of Organic Chemistry, 1988 , vol. 53, # 13 p. 2916 - 2920

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被引用次数: 142

摘要

Diisopinocampheylchloroborane, dIpc2BC1, reduces ring and chain substituted haloaralkyl ketones to the corresponding halo alcohols in excellent enantiomeric excess. In certain cases these alcohols can be upgraded by simple methods to essentially 100% ee. For instance,(+)-or (-)-3-chlorc-l-phenyl-l-propanol is initially obtained in 97% ee. Simple recrystallization then furnishes the pure enantiomers. These chiral halo alcohols are ...