Premium
N ‐(Diazoacetyl)oxazolidin‐2‐thiones as Sulfur‐Donor Reagents: Asymmetric Synthesis of Thiiranes from Aldehydes
Author(s) -
Cano Israel,
GómezBengoa Enrique,
Landa Aitor,
Maestro Miguel,
Mielgo Antonia,
Olaizola Iurre,
Oiarbide Mikel,
Palomo Claudio
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204771
Subject(s) - stereocenter , diazo , chemistry , cycloaddition , sulfur , reagent , adduct , stereoselectivity , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
Sulfur tyranny : Thiiranes, instead of oxiranes, can be obtained in a highly stereoselective manner through the cycloaddition reaction of N ‐acyl oxazolidine tethered diazo thione compounds with aldehydes catalyzed by Rh II . Thus, this reaction provides versatile adducts S functionalized at both the α and β position, with concomitant generation of two contiguous stereocenters.