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Synlett 2007(17): 2762-2763  
DOI: 10.1055/s-2007-991074
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

(-)-Diisopinocampheyl Chloroborane [(-)-DIP-ChlorideTM]: A Versatile Reagent in Asymmetric Synthesis

Peng Zhang*
College of Chemistry & Material Science, Hebei Normal ­University, Shijiazhuang 050016, P. R. of China
e-Mail: orgsynchem@126.com;
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Publication History

Publication Date:
25 September 2007 (online)

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Introduction

Since its introduction in 1985, [1] (-)-diisopinocampheyl chloroborane [(-)-DIP-ChlorideTM] has become one of the most effective reagents in asymmetric synthesis for the reduction of prochiral ketones. [2] It exhibits the phenomenon of asymmetric amplification in this reduction reaction. [3] The types of ketones delivering high enantioselectivity upon DIP-ChlorideTM are aralkyl, [4] hindered alkynyl, [5] ­trifluoromethyl, [6] α-acetylenic α′-fluoroalkyl, [7] α-fluoro­methyl, [8] benzofuryl halomethyl, [9] olefinic, and cyclic ­ketones. [10] 2-Amino acetophenones, [11] ortho-substituted benzophenones, [12] 1,2- and 1,3-hydroxy ketones, [13] aliphatic acylsilanes, [14] 2-acetylbenzofuran, [15] and α-oxocarboxylic acids [16] have also been asymmetrically reduced with high enantiomeric excess using this reagent. This reagent has also been applied in key steps in the preparation of several important pharmaceutical compounds such as antidepressant fluoxetine hydrochloride, [17] a selective D1 agonist, [18] PAF-antagonists L-659,989 [19] and MK-287, [20] Dolastatin 10, [21] a potential antipsychotic and broncho­dilator, [22] (-)-Lobeline, [23] and an LTD4 antagonist. [24] It is found to be a useful reagent in the synthesis of chiral ligands [25] and is also capable of effecting asymmetric aldol reactions. [26]