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First asymmetric synthesis of 3‐alkoxycarbonyl‐2‐amino‐4‐aryl‐4 H ‐naphtho[1,2‐ b ]pyrans
Author(s) -
Martín Nazario,
MartínezGrau Angeles,
Seoane Carlos,
Marco José L.,
Albert Armando,
Cano Félix H.
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330105
Subject(s) - chemistry , diastereomer , pyran , conjugate , aryl , stereochemistry , enantioselective synthesis , michael reaction , absolute configuration , organic chemistry , catalysis , mathematical analysis , alkyl , mathematics
Abstract The first asymmetric synthesis of 3‐alkoxycarbonyl‐2‐amino‐4‐aryl‐4 H ‐naphtho[1,2‐ b ]pyrans, by Michael addition of 1‐naphthol to chirally modified arylidenecyanoacetates 6 and 7 , is described. Good yields and low diastereomeric excesses have been obtained in the 1,4‐conjugate additions. The absolute stereochemistry at C‐4 in major isomers of pyrans 8 and 9 has been assigned as 5 by X‐ray analysis of major pyran 8 .