7306-12-9Relevant academic research and scientific papers
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.
