Do the electronic effects of sulfur indeed control the x-selectivity of γ-sulfenyl enones? Further evidence

Ganesh Babu, K. ; Yadav, Veejendra K. (2007) Do the electronic effects of sulfur indeed control the x-selectivity of γ-sulfenyl enones? Further evidence Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 46 (6). pp. 1001-1003. ISSN 0376-4699

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Abstract

The reductions of γ-sulfenyl and γ-sulfonyl enones with NaBH4 and LiAlH4 lead to highly reduced anti-to-S selectivity. The selectivity turns even syn-to-S in some instances. These results underline the significance of steric effects arising from the steric bulk of the reducing agent and the substituent on S and negate any substantial role of the electronic effects of S on the observed diastereocontrol as reported previously.

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Deposited On:12 Mar 2012 07:28
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