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Enantioselective Synthesis of (−)‐( R )‐Cordiachromene and (−)‐( R )‐Dictyochromenol Utilizing Intramolecular S N Ar Reaction
Author(s) -
Noda Yoshihiro,
Yasuda Misato
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200312
Subject(s) - enantioselective synthesis , chemistry , intramolecular force , chirality (physics) , stereochemistry , ring (chemistry) , catalysis , combinatorial chemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
A simple and efficient enantioselective synthesis of chromene, (−)‐( R )‐cordiachromene ( 1 ), and (−)‐( R )‐dictyochromenol ( 2 ) has been accomplished. This convergent synthesis utilizes intramolecular S N Ar reaction for the formation of chroman ring, and Seebach 's method of ‘ self‐reproduction of chirality ’ should establish the ( R )‐configuration of the C(2) side chain as key steps.