Long‐Range Electrostatic Effects in Synthesis: Dipole‐Controlled Nucleophilic Addition to a Naphthoquinone Acetal in Model Studies toward Diepoxin σ | Zendy

Wipf Peter | Zendy; Jung JaeKyu | Zendy

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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.

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