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The Synthesis of Chiral Benzothiazine and Thiazinoquinoline Derivatives
Author(s) -
Wang Long,
Priebbenow Daniel L.,
Chen Xiao Yun,
Pan FangFang,
Bolm Carsten
Publication year - 2015
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.201500250
Subject(s) - benzothiazine , enantiopure drug , chemistry , aldol reaction , derivative (finance) , enantioselective synthesis , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , financial economics , economics
Abstract The syntheses of a series of enantiopure conformationally restricted benzothiazine and thiazinoquinoline derivatives are presented. Key starting materials are 3‐aminoacetophenone and ( S )‐ S ‐methyl‐ S ‐phenylsulfoximine. By using a short reaction sequence, the 8‐amino‐2,1‐benzothiazine derivative was readily prepared, which served as a valuable intermediate for the synthesis of additional derivatives. Initial experiments show that employing such compounds in copper‐catalyzed asymmetric Mukaiyama‐type aldol reactions provided products with moderate enantioselectivity.