TY - JOUR
T1 - Asymmetric [2,3]-Wittig rearrangement as a general tool for asymmetric synthesis
AU - Nakai, Takeshi
AU - Tomooka, Katsuhiko
N1 - Funding Information:
This work is the result of experimental and intellectualcontributions by many co-workers who are listed in the references. The [2,3]-Wittig project hm been supported over the years by the Grant-in-Aids for Scientific Research from the Ministry of Education, Science and Culture, Japan.
PY - 1997/3
Y1 - 1997/3
N2 - Recent advances in the asymmetric [2,3]-Wittig rearrangement as a general tool for asymmetric synthesis of homoallylic alcohols are described. First, the synthetic utilities of the asymmetric transmission type and the two asymmetric induction types are demonstrated, including applications in asymmetric syntheses of natural products and steroid side chains. Second, some examples are presented of the enantioselective versions involving a chiral ligand-bound boron enolate and organolithium as the migrating terminus. Finally, the mechanistic grounds of the asymmetric versions are discussed on the basis of the stereochemical analyses of the asymmetric version involving an enantiomerically-defined carbanion terminus.
AB - Recent advances in the asymmetric [2,3]-Wittig rearrangement as a general tool for asymmetric synthesis of homoallylic alcohols are described. First, the synthetic utilities of the asymmetric transmission type and the two asymmetric induction types are demonstrated, including applications in asymmetric syntheses of natural products and steroid side chains. Second, some examples are presented of the enantioselective versions involving a chiral ligand-bound boron enolate and organolithium as the migrating terminus. Finally, the mechanistic grounds of the asymmetric versions are discussed on the basis of the stereochemical analyses of the asymmetric version involving an enantiomerically-defined carbanion terminus.
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U2 - 10.1351/pac199769030595
DO - 10.1351/pac199769030595
M3 - Article
AN - SCOPUS:0001251247
SN - 0033-4545
VL - 69
SP - 595
EP - 600
JO - Pure and Applied Chemistry
JF - Pure and Applied Chemistry
IS - 3
ER -