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Issue 22, 2011
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Iridium-catalyzed asymmetric allylation of sodium triisopropylsilanethiolate: A new way to form chiral thiols

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Abstract

The iridium phosphoramidite complex-promoted regio- and enantioselective reaction of allylic carbonates with sodium triisopropylsilanethiolate produced allylic sulfides in 40–77% yields with up to 97 : 3 (branched : linear) and 89% ee, which were readily transformed into chiral thiol in 68% yield with 87% ee or disulfides with two chiral C–S bond centers in 40–73% yields with up to 90 : 10 dr and 99% ee.

Graphical abstract: Iridium-catalyzed asymmetric allylation of sodium triisopropylsilanethiolate: A new way to form chiral thiols

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Publication details

The article was received on 05 Aug 2011, accepted on 25 Aug 2011 and first published on 25 Aug 2011


Article type: Paper
DOI: 10.1039/C1OB06332D
Org. Biomol. Chem., 2011,9, 7897-7903

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    Iridium-catalyzed asymmetric allylation of sodium triisopropylsilanethiolate: A new way to form chiral thiols

    W. Huang, S. Zheng, J. Tang and X. Zhao, Org. Biomol. Chem., 2011, 9, 7897
    DOI: 10.1039/C1OB06332D

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