Issue 8, 2016

Re-orienting coupling of organocuprates with propargyl electrophiles from SN2′ to SN2 with stereocontrol

Abstract

Diorganocuprate(I) reagents derived from lithiated heterocycles and CuCN react with enantioenriched secondary propargyl bromides to give the corresponding propargylated heterocycles. While propargyl electrophiles typically undergo SN2′ displacement, this transformation represents the first example of the reaction of hard carbanions with propargyl electrophiles in an SN2 fashion and occurs with excellent levels of stereoinversion. The new method was applied to the formal synthesis of (+)-frondosin B.

Graphical abstract: Re-orienting coupling of organocuprates with propargyl electrophiles from SN2′ to SN2 with stereocontrol

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Mar 2016
Accepted
09 May 2016
First published
10 May 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 4985-4989

Author version available

Re-orienting coupling of organocuprates with propargyl electrophiles from SN2′ to SN2 with stereocontrol

B. M. Trost and L. Debien, Chem. Sci., 2016, 7, 4985 DOI: 10.1039/C6SC01086E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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