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Asymmetric Photocycloaddition in Solution of a Chiral Crystallized Naphthamide
Author(s) -
Sakamoto Masami,
Unosawa Atsushi,
Kobaru Shuichiro,
Saito Ayako,
Mino Takashi,
Fujita Tsutomu
Publication year - 2005
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.200501156
Subject(s) - chirality (physics) , chemistry , crystallography , stereochemistry , physics , chiral symmetry , particle physics , nambu–jona lasinio model , quark
Frozen chirality : Achiral naphthamide 1 can be crystallized to give chiral 1* , whose chiral molecular conformation is retained (“frozen”) after the crystals are dissolved in cold THF. Asymmetric photocycloaddition of 1* with 9‐cyanoanthracene (9‐CNAN) in solution gives cycloadduct 2 with high enantioselectivity.