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Formation of Enantiomerically Pure 1‐Fluorovinyl and 1‐Fluoromethyl Sulfoxides
Author(s) -
van Steenis Jan Hein,
Boer Philip W. S.,
van der Hoeven Harald A.,
van der Gen Arne
Publication year - 2001
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(200103)2001:5<911::aid-ejoc911>3.0.co;2-q
Subject(s) - chemistry , stereoselectivity , enantiomer , solvolysis , wittig reaction , organic chemistry , oxide , medicinal chemistry , stereochemistry , catalysis , hydrolysis
( S S )‐[Fluoro( p ‐tolylsulfinyl)methyl]diphenylphosphane oxide ( 2 ) was obtained with complete stereoselectivity from (fluoromethyl)diphenylphosphane oxide ( 3 ) and ( S )‐(−)‐menthyl p ‐toluenesulfinate. 1‐Fluorovinyl p ‐tolyl sulfoxides 1 were prepared in good yields by Horner−Wittig reaction of 2 with aldehydes, in excellent enantiomeric excess ( ee ). With ketones, yields were generally low. Stereoselectivity was high for aliphatic aldehydes, producing ( Z ) isomers, and for benzaldehydes, yielding the ( E ) isomers. A two‐step, one‐pot procedure for the conversion of 3 into 1 was also developed. Solvolysis of 2 provided the first route to enantiomerically pure ( S )‐1‐(fluoromethyl)sulfinyl‐4‐methylbenzene ( 7 ).