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Issue 31, 2015
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Effective 1,5-stereocontrol in Pd(0)/InI promoted reactions of chiral N-Ts-4-vinylazetidin-2-ones with aldehydes. An efficient entry into nonracemic semi-protected (3Z)-2,6-anti-enediols

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Abstract

ε-Amido-allylindiums generated in situ from N-Ts-4-vinylazetidin-2-ones in the presence of 2 eq. of InI and catalytic amounts of Pd(PPh3)4 react with a number of aromatic and aliphatic aldehydes with effective remote 1,5-stereocontrol to afford (3Z)-2,6-anti-enediols as major products in good yields and with excellent diastereoselectivity.

Graphical abstract: Effective 1,5-stereocontrol in Pd(0)/InI promoted reactions of chiral N-Ts-4-vinylazetidin-2-ones with aldehydes. An efficient entry into nonracemic semi-protected (3Z)-2,6-anti-enediols

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Supplementary files

Article information


Submitted
17 Feb 2015
Accepted
11 Mar 2015
First published
11 Mar 2015

Chem. Commun., 2015,51, 6796-6799
Article type
Communication

Effective 1,5-stereocontrol in Pd(0)/InI promoted reactions of chiral N-Ts-4-vinylazetidin-2-ones with aldehydes. An efficient entry into nonracemic semi-protected (3Z)-2,6-anti-enediols

U. K. Klimczak and B. K. Zambroń, Chem. Commun., 2015, 51, 6796
DOI: 10.1039/C5CC01485A

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