Accession Number : ADA193710

Title :   Super Hydrides.

Descriptive Note : Final rept. 15 Mar 85-14 Mar 88,

Corporate Author : PURDUE UNIV LAFAYETTE IN

Personal Author(s) : Brown, Herbert C

PDF Url : ADA193710

Report Date : Mar 1988

Pagination or Media Count : 27

Abstract : The discovery of metal hydride reducing reagents has without exaggeration revolutionized the reduction of functional groups in organic chemistry. In the last decade or so asymmetric synthesis has emerged from the cold to vie quite successfully with enzymes as a means of incorporating chirality in prostereogenic centers. My group has been in the forefront of this second revolution in organic chemistry. During the course of our research for the period covered in this Final Report, we have made tremendous leaps forward, both in developing new chiral reducing reagents and in understanding their mode of reaction. In this regard we have concentrated our efforts in two major areas, (1) Chiral trialkylboranes and (2) Chiral borohydrides. In the first case we have discovered the extremely versatile and readily accessible asymmetric reducing reagent, diisopinocampheylchloroborane, Ipc2BCl, derivable from alpha-pinene of either antipode. Our success with Ipc2BCl in transferring stereogenicity to alcohols encouraged us to explore further modifications of the alpha-pinene moiety as useful chiral directors.

Descriptors :   *BOROHYDRIDES, *BORANES, *REDUCTION(CHEMISTRY), ALCOHOLS, ASYMMETRY, ENZYMES, HYDRIDES, ORGANIC CHEMISTRY, REDUCTION, SYNTHESIS(CHEMISTRY), ALKYL RADICALS

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE