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On the Stereoselectivity of Alkenoxyl Radical 6‐ exo ‐ trig Cyclizations
Author(s) -
Schneiders Nina,
Gottwald Thomas,
Hartung Jens
Publication year - 2009
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.200801116
Subject(s) - chemistry , stereoselectivity , tetrahydropyran , radical , ring (chemistry) , stereochemistry , closure (psychology) , radical cyclization , organic chemistry , catalysis , economics , market economy
The investigated set of 6‐ exo ‐ trig cyclizations occurs irreversibly and justifies the use of tetrahydropyran‐derived transition structures for rationalizing 2,6‐ cis , 2,5‐ trans , and 2,4‐ cis stereoselectivity in ring‐closure reactions of 1‐, 2‐, and 3‐phenyl‐6‐methyl‐5‐hepten‐1‐oxyl radicals. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)