Journal of Organic Chemistry 83.4 (2018): 1940-1947
ISSN:0022-3263 (print); 1520-6904 (online)
DOI:10.1021/acs.joc.7b02887
Funded by:We thank DGAPA-UNAM (project number PAPIITIN205316) for financial support. Financial support from the Spanish Government (CTQ2015-64561-R) is also gratefully acknowledged
The generation of diastereomerically enriched secondary benzyl propargyl alcohols by the asymmetric addition of ortho-sulfinylbenzyl carbanions to sulfonylacetylene derivatives via formation of a Csp-Csp 3 bond is described. This reaction proceeds through an unusual α-attack (anti-Michael addition) of the ortho-sulfinylbenzyl carbanions, followed by elimination of the arylsulfonyl moiety. The scope of this alkynylation reaction is also discussed. Moreover, the development of a new approach for the synthesis of optically active tertiary benzylpropargyl alcohols is described, discussing the possible stereocourse of the reaction so as the influence of the ether 18-crown-6 and steric importance of acetylenic substituent