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Asymmetric Synthesis of β‐Amino‐α‐hydroxy Aldehyde Derivatives Bearing a Quaternary Stereogenic Center
Author(s) -
Drelich Piotr,
Skrzyńska Anna,
Albrecht Łukasz
Publication year - 2016
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/ejoc.201600872
Subject(s) - stereocenter , chemistry , aldehyde , moiety , chemoselectivity , acetal , stereoselectivity , reagent , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis
An organocatalytic approach for the stereoselective synthesis of β‐amino‐α‐hydroxy aldehydes bearing a fully substituted stereogenic center in the α‐position with respect to the aldehyde moiety is presented. It utilizes a one‐pot reaction cascade involving an aziridination reaction followed by a sodium methoxide initiated rearrangement. In order to control the chemoselectivity of the rearrangement, a new aziridinating reagent enabling the introduction of a nosyl protecting group at the nitrogen atom has been designed and introduced. Products of the reaction have thus been obtained exclusively as dimethyl acetal. The possibility to deprotect the aldehyde moiety with the preservation of the introduced optical purity has also been demonstrated.