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https://hdl.handle.net/2440/43990
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Type: | Journal article |
Title: | Stereoselective reductions of N-Boc-hexahydro-1H-indolin-5(6H)-ones |
Author: | Brodney, M. Cole, M. Freemont, J. Kyi, S. Junk, P. Padwa, A. Riches, A. Ryan, J. |
Citation: | Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry, 2007; 48(11):1939-1943 |
Publisher: | Pergamon-Elsevier Science Ltd |
Issue Date: | 2007 |
ISSN: | 0040-4039 |
Statement of Responsibility: | Michael A. Brodney, Marcus L. Cole, Jamie A. Freemont, Stella Kyi, Peter C. Junk, Albert Padwa, Andrew G. Riches and John H. Ryan |
Abstract: | We report the divergent effects of a 3a-methyl and 3a-phenyl substituent on the chemoselectivity and stereoselectivity of reduction of the enamide moiety of N-Boc-hexahydro-1H-indolin-5(6H)-ones. Under ionic reduction conditions (triethylsilane/trifluoroacetic acid) the enamide group of 3a-methyl-N-Boc-hexahydro-1H-indolin-5(6H)-one was reduced to afford exclusively a cis ring-fused product. For the 3a-phenyl substituted analogue more forcing conditions (sodium cyanoborohydride at pH 2–2.5) were required and resulted in the selective reduction of the enamide group to give a trans ring-fused product as well as reduction of the ketone group. |
Description: | Copyright © 2007 Elsevier Ltd All rights reserved. |
DOI: | 10.1016/j.tetlet.2007.01.078 |
Description (link): | http://www.elsevier.com/wps/find/journaldescription.cws_home/233/description#description |
Published version: | http://dx.doi.org/10.1016/j.tetlet.2007.01.078 |
Appears in Collections: | Aurora harvest 6 Chemistry publications |
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