7306-12-9Relevant articles and documents
Stereoselective reductions of N-Boc-hexahydro-1H-indolin-5(6H)-ones
Brodney, Michael A.,Cole, Marcus L.,Freemont, Jamie A.,Kyi, Stella,Junk, Peter C.,Padwa, Albert,Riches, Andrew G.,Ryan, John H.
, p. 1939 - 1943 (2007/10/03)
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.
REACTION OF 4- AND 4,4-SUBSTITUTED 1,3-DIOXANES WITH ETHYL ACETATE
Rakhmankulov, I. L.,Kantor, E. A.,Rakhmankulov, D. L.
, p. 1093 - 1097 (2007/10/02)
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