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Diastereo‐ and Enantioselective Synthesis of 1,2,3‐Substituted Cyclopropanes with Zinc Carbenoids
Author(s) -
Charette André B.,
Lemay Jacinthe
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.199710901
Subject(s) - enantioselective synthesis , enantiomer , chemistry , reagent , zinc , solvent , organic chemistry , cyclopropanation , natural product , combinatorial chemistry , catalysis
Substituted, functionalized iodoalkylzinc reagents in combination with the chiral dioxaborolane 2 give excellent diastereo‐ and enantiomeric selectivities in cyclopropanations when substituted allyl alcohols 1 (R 1 H, Et, CH 2 OBn; R 2 H, Ph, n Pr; R 3 H, Me) are used as starting materials and CH 2 Cl 2 as solvent. This efficient preparation of chiral, nonracemic 1,2,3‐trisubstituted cyclopropanes 3 might be useful in natural product synthesis.