Dramatic Acceleration of an Acyl Transfer-Initiated Cascade by Using Electron-Rich Amidine-Based Catalysts

Nicholas A. Ahlemeyer; Emma V. Streff; Pandi Muthupandi; Vladimir B. Birman

doi:10.1021/acs.orglett.7b03044

Dramatic Acceleration of an Acyl Transfer-Initiated Cascade by Using Electron-Rich Amidine-Based Catalysts

Nicholas A. Ahlemeyer
, Emma V. Streff
, Pandi Muthupandi
, Vladimir B. Birman

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

32 Scopus citations

Abstract

A tandem rearrangement of α,β-unsaturated thioesters into tricyclic ene-lactones fails with conventional amidine-based catalysts, but becomes possible when their electron-rich analogs are employed. A highly diastereo- and enantioselective version of this process has been developed using H-PIP 1b, a chiral catalyst prepared over a decade ago, but never utilized since its disclosure.

Original language	English
Pages (from-to)	6486-6489
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.7b03044
State	Published - Dec 15 2017

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abstract = "A tandem rearrangement of α,β-unsaturated thioesters into tricyclic ene-lactones fails with conventional amidine-based catalysts, but becomes possible when their electron-rich analogs are employed. A highly diastereo- and enantioselective version of this process has been developed using H-PIP 1b, a chiral catalyst prepared over a decade ago, but never utilized since its disclosure.",

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AU - Muthupandi, Pandi

AU - Birman, Vladimir B.

PY - 2017/12/15

Y1 - 2017/12/15

N2 - A tandem rearrangement of α,β-unsaturated thioesters into tricyclic ene-lactones fails with conventional amidine-based catalysts, but becomes possible when their electron-rich analogs are employed. A highly diastereo- and enantioselective version of this process has been developed using H-PIP 1b, a chiral catalyst prepared over a decade ago, but never utilized since its disclosure.

AB - A tandem rearrangement of α,β-unsaturated thioesters into tricyclic ene-lactones fails with conventional amidine-based catalysts, but becomes possible when their electron-rich analogs are employed. A highly diastereo- and enantioselective version of this process has been developed using H-PIP 1b, a chiral catalyst prepared over a decade ago, but never utilized since its disclosure.

UR - https://www.scopus.com/pages/publications/85038410878

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ER -

Dramatic Acceleration of an Acyl Transfer-Initiated Cascade by Using Electron-Rich Amidine-Based Catalysts

Abstract

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