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Elsevier, Tetrahedron Letters, 11(48), p. 1939-1943

DOI: 10.1016/j.tetlet.2007.01.078

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Stereoselective reductions of N-Boc-hexahydro-1H-indolin-5(6H)-ones

Journal article published in 2007 by Michael A. Brodney, Marcus L. Cole, Jamie A. Freemont, Stella Kyi, Peter C. Junk ORCID, Albert Padwa, Andrew G. Riches, John H. Ryan
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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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. ; http://www.elsevier.com/wps/find/journaldescription.cws_home/233/description#description ; Michael A. Brodney, Marcus L. Cole, Jamie A. Freemont, Stella Kyi, Peter C. Junk, Albert Padwa, Andrew G. Riches and John H. Ryan ; Copyright © 2007 Elsevier Ltd All rights reserved.