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Long‐Range Electrostatic Effects in Synthesis: Dipole‐Controlled Nucleophilic Addition to a Naphthoquinone Acetal in Model Studies toward Diepoxin σ
Author(s) -
Wipf Peter,
Jung JaeKyu
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199707641
Subject(s) - steric effects , nucleophile , naphthoquinone , chemistry , selectivity , acetal , 1,4 naphthoquinone , nucleophilic addition , stereochemistry , combinatorial chemistry , computational chemistry , organic chemistry , catalysis
Trifluoromethylacetal groups as chiral auxiliaries enhance diastereoselectivity in nucleophilic additions to benzo‐ and naphthoquinone derivatives. In the methylation of 1 to give 2 and 3 facial selectivity is induced not by steric effects but by long‐range electrostatic effects. This principle may be used in the design of a new class of chiral auxiliaries.