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

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...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-04, Vol.51 (31), p.6796-6799
Main Authors: Klimczak, Urszula K, Zambroń, Bartosz K
Format: Article
Language:English
Subjects:
Aldehydes
Aliphatic compounds
Catalysis
Catalysts
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc01485a