Tetrahedron letters

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

MA Brodney, ML Cole, JA Freemont, S Kyi, PC Junk…

Index: Brodney, Michael A.; Cole, Marcus L.; Freemont, Jamie A.; Kyi, Stella; Junk, Peter C.; Padwa, Albert; Riches, Andrew G.; Ryan, John H. Tetrahedron Letters, 2007 , vol. 48, # 11 p. 1939 - 1943

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Citation Number: 4

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 ...