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Regio‐ and Stereoselective Carbosulfenylation of Olefins
Author(s) -
Reetz Manfred T.,
Seitz Thomas
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198710281
Subject(s) - stereoselectivity , stereospecificity , chemistry , reagent , asymmetric induction , alkylation , lewis acids and bases , stereochemistry , organic chemistry , medicinal chemistry , enantioselective synthesis , catalysis
In a one‐pot procedure, cyclic olefins such as 1 , n = 1–3, can be transformed stereospecifically into the trans ‐substituted products 2 by chlorosulfenylation followed by alkylation with Lewis acidic organometallic reagents such as (CH 3 ) 2 Zn/TiCl 4 or (CH 3 ) 3 Al. This reaction concept can be extended to trisubstituted olefins and α‐chiral 1,2‐disubstituted olefins, such as 3 , high regio‐ and stereoselectivity being achieved in the latter case (formation of 4 ). The interplay of 1,2‐asymmetric induction and trans stereospecificity leads to defined 1,3‐stereorelationships.