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Stereoselective Synthesis of ( E )‐Vinyl Sulfoxides by the Horner−Wittig Reaction
Author(s) -
van Steenis Jan Hein,
van Es Joseph Johannes Gerardus Steven,
van der Gen Arne
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200008)2000:15<2787::aid-ejoc2787>3.0.co;2-z
Subject(s) - chemistry , wittig reaction , stereoselectivity , organic chemistry , combinatorial chemistry , catalysis
The Horner−Wittig reaction of sulfinylmethyl‐substituted diphenylphosphane oxides 1 − 3 with aldehydes is reported. In a straightforward synthesis, ( E )‐vinyl sulfoxides 4 (R 1 = Ph), 5 (R 1 = Me) and 6 (R 1 = p Tol) were formed, mostly with high configurational selectivity and in high yields. In less selective cases, the ( E )/( Z ) ratio could be improved by slightly modifying the procedure. The use of ( S S )‐(+)‐diphenyl( p ‐tolylsulfinylmethyl)phosphane oxide ( 3 ) allowed the synthesis of enantiomerically pure ( E )‐vinyl sulfoxides.