Stereoselective reductions of substituted cyclohexyl and cyclopentyl carbon-nitrogen. pi. systems with hydride reagents

…, R Sivakumar, F Cistone, YP Stercho

Index: Hutchins, Robert O.; Su, Wei-Yang; Sivakumar, Ramachandran; Cistone, Frank; Stercho, Yuriy P. Journal of Organic Chemistry, 1983 , vol. 48, # 20 p. 3412 - 3422

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Citation Number: 108

Abstract

Reductions of 3-and 4-substituted cyclohexyl imines, iminium salts, and enamines (via iminium ions) with various hydride reagents reveal that while small reagents (NaBH,, NaBH3CN) favor axial approach as observed with the corresponding ketones, even moderately bulky reagents (ie, acetoxyboranes) attack preferentially from the equatorial side. This is in direct contrast to the results observed for the same reagents with the ...

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