Highly Stereoselective Synthesis of Multisubstituted Olefins from Alkynyl Tetracoordinate Borons and Iodonium Ylides via a Cyclic Intermediate

We developed an intriguing and practical strategy for highly stereoselective assembly of multisubstituted olefins from alkynyl tetracoordinate boron species via a cyclic intermediate with 1,2-phenyl migration. We also developed a general method for the construction of deuterated trisubstituted alken...

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Bibliographic Details
Published in:Organic letters 2024-05, Vol.26 (18), p.3872-3877
Main Authors: Liang, Jinchao, Chen, Xin, Chen, Jinglong, Ma, Xingxing, Song, Qiuling
Format: Article
Language:English
Subjects:
alkenes
boron
reaction mechanisms
species
stereoselective synthesis
stereoselectivity
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Summary:We developed an intriguing and practical strategy for highly stereoselective assembly of multisubstituted olefins from alkynyl tetracoordinate boron species via a cyclic intermediate with 1,2-phenyl migration. We also developed a general method for the construction of deuterated trisubstituted alkenes from a cheap deuteration source, D2O, and the corresponding deuterated trisubstituted alkenes were obtained with excellent deuteration rates. This transformation features a novel reaction mechanism, exclusive stereoselectivity, and deuterated trisubstituted alkenes with excellent deuteration ratios.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01031