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Transition‐Metal‐Catalyzed Carbenoid Reactions of Sulfonium Ylides
Author(s) -
Müller Paul,
Fernandez Daniel,
Nury Patrice,
Rossier JeanClaude
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990609)82:6<935::aid-hlca935>3.0.co;2-x
Subject(s) - carbenoid , chemistry , cyclopropanation , ylide , ethyl diazoacetate , sulfonium , catalysis , cyclopropane , transition metal , medicinal chemistry , organic chemistry , rhodium , ring (chemistry) , salt (chemistry)
Olefins undergo cyclopropanation with diphenylsulfonium (ethoxycarbonyl)methylide (=diphenylsulfonium 2‐ethoxy‐2‐oxoethylide; 3a ) in the presence of chiral Cu I or Rh II catalysts. trans/cis Ratios and ee's of the cyclopropanes 6 obtained with this ylide in the presence of a chiral Cu I catalyst 7 are identical with those obtained with ethyl diazoacetate ( 4 ). In the case of catalysis with Rh II , the trans / cis ratios of the cyclopropanes as well as the enantioselectivity change slightly upon going from the ylide 3a to diazoacetate 4 .