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Cuprates as Selective Metalating Reagents for Aromatic Halides
Author(s) -
Kondo Yoshinori,
Matsudaira Tetsuji,
Sato Junko,
Murata Naoko,
Sakamoto Takao
Publication year - 1996
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.199607361
Subject(s) - regioselectivity , chemistry , reagent , moiety , epoxide , intramolecular force , enantiomer , halide , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Regioselective reactions with almost no decrease in enantiomeric purity : the 5‐ exo ( 2 ) and 6‐ endo ( 3 ) cyclization products are formed from epoxide 1 on reaction with [Li 3 ZnMe 3 (SCN) 2 ] and [Li 3 Cu(CN)Me 3 ], respectively. No further reagents are needed. Halogen – metal exchange of 1 with the appropriate ate complex and subsequent intramolecular epoxide opening by the arylcuprate moiety results in the asymmetric synthesis of 2 and 3 , potential precursors of the antibiotics CC‐1065 and duocarmycin.
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