Chiral α,β-Dialkoxy- and α-Alkoxy-β-aminostannanes: Preparation and Copper-Mediated Cross-Coupling

Suchismita Acharya, A. Bandyopadhyay, D. K. Barma, Jorge H. Capdevila, J. R. Falck

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

(Equation Presented) Addition of Zn(n-Bu3Sn)2 to prochiral aldehydes affords anti-α,β-dialkoxy- and anti-α-alkoxy-β-aminostannanes in good yield (up to 77%) and excellent diastereoselectivity (up to 98% de), syn-lsomers are accessed from the initial adducts via Mitsunobu inversion/saponification. The corresponding thionocarbamates undergo mild Cu(l)-mediated cross-coupling with a variety of organic halides, inter alia, allylic, cinnamylic, propargylic, and acetylenic, with retention of configuration.

Original languageEnglish
Pages (from-to)4759-4762
Number of pages4
JournalOrganic Letters
Volume5
Issue number25
DOIs
StatePublished - 11 Dec 2003

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