N ‐(Diazoacetyl)oxazolidin‐2‐thiones as Sulfur‐Donor Reagents: Asymmetric Synthesis of Thiiranes from Aldehydes | Zendy

Cano Israel | Zendy; GómezBengoa Enrique | Zendy; Landa Aitor | Zendy; Maestro Miguel | Zendy; Mielgo Antonia | Zendy; Olaizola Iurre | Zendy; Oiarbide Mikel | Zendy; Palomo Claudio | Zendy

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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.

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