Premium
Unusual Regioselectivity in the Reductive Coupling of Alkynes and Allenes by Hydrozirconation and Zinca‐Claisen Rearrangement
Author(s) -
Suzuki Keisuke,
Imai Takahiro,
Yamanoi Shigeo,
Chino Masao,
Matsumoto Takashi
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.199724691
Subject(s) - regioselectivity , chemistry , adduct , claisen rearrangement , zirconium , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The α‐adduct is the sole product of the coupling of vinyl‐ and allylzirconium compounds with ZnCl 2 (see below), provided no Mg II salts are present. The zirconium compounds are formed in situ from alkynes and allenes, and the overall reaction opens a new preparative route to the vitamin E side chain through asymmetric induction in the 1,5‐position. R 1 = CH 2 OCPh 3 , R 2 = CHMeCH 2 OCH 2 OMe, “Zr” = [Cp 2 Zr(H)Cl].