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Stereochemistry and Construction of Tetrasubstituted Chiral Carbon Centers in Intramolecular Pd‐Catalyzed 1,3‐Chirality Transfer Reactions
Author(s) -
Kawai Nobuyuki,
Lagrange JeanMarie,
Uenishi Jun'ichi
Publication year - 2007
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.200601103
Subject(s) - chemistry , chirality (physics) , allylic rearrangement , intramolecular force , catalysis , asymmetric carbon , stereochemistry , organic chemistry , optically active , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
A Pd II ‐catalyzed cyclization for the construction – from chiral allylic alcohols – of tetrahydropyrans containing tetrasubstituted chiral carbons proceeded stereospecifically by 1,3‐chirality transfer through a syn ‐S N 2′ type process. The chiral 2,2,6‐trisubstituted tetrahydropyrans 5 and spiro hydropyrans 6 were obtained in high yields under mild reaction conditions.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)