[1,2]-Wittig rearrangement of enantio-defined α-alkoxyalkyllithiums: Structural requirement and steric course at the Li-bearing terminus.

Katsuhiko Tomooka, Tatsuya Igarashi, Takeshi Nakai

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

The [1,2]-Wittig rearrangements of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs, generated from the enantio-enriched stannanes via Sn / Li exchange, are shown to proceed predominantly with inversion of configuration at the Li-bearing terminus and retention of configuration at the migrating center, and exhibit a significant level of mutual enantiomer recognition in the radical recombination process.

Original languageEnglish
Pages (from-to)5927-5932
Number of pages6
JournalTetrahedron
Volume50
Issue number20
DOIs
Publication statusPublished - 1994

Fingerprint

Bearings (structural)
Enantiomers
Genetic Recombination
stannane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

[1,2]-Wittig rearrangement of enantio-defined α-alkoxyalkyllithiums : Structural requirement and steric course at the Li-bearing terminus. / Tomooka, Katsuhiko; Igarashi, Tatsuya; Nakai, Takeshi.

In: Tetrahedron, Vol. 50, No. 20, 1994, p. 5927-5932.

Research output: Contribution to journalArticle

@article{27d1ca9ff61842c49aec372eae3bb972,
title = "[1,2]-Wittig rearrangement of enantio-defined α-alkoxyalkyllithiums: Structural requirement and steric course at the Li-bearing terminus.",
abstract = "The [1,2]-Wittig rearrangements of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs, generated from the enantio-enriched stannanes via Sn / Li exchange, are shown to proceed predominantly with inversion of configuration at the Li-bearing terminus and retention of configuration at the migrating center, and exhibit a significant level of mutual enantiomer recognition in the radical recombination process.",
author = "Katsuhiko Tomooka and Tatsuya Igarashi and Takeshi Nakai",
year = "1994",
doi = "10.1016/S0040-4020(01)90447-8",
language = "English",
volume = "50",
pages = "5927--5932",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "20",

}

TY - JOUR

T1 - [1,2]-Wittig rearrangement of enantio-defined α-alkoxyalkyllithiums

T2 - Structural requirement and steric course at the Li-bearing terminus.

AU - Tomooka, Katsuhiko

AU - Igarashi, Tatsuya

AU - Nakai, Takeshi

PY - 1994

Y1 - 1994

N2 - The [1,2]-Wittig rearrangements of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs, generated from the enantio-enriched stannanes via Sn / Li exchange, are shown to proceed predominantly with inversion of configuration at the Li-bearing terminus and retention of configuration at the migrating center, and exhibit a significant level of mutual enantiomer recognition in the radical recombination process.

AB - The [1,2]-Wittig rearrangements of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs, generated from the enantio-enriched stannanes via Sn / Li exchange, are shown to proceed predominantly with inversion of configuration at the Li-bearing terminus and retention of configuration at the migrating center, and exhibit a significant level of mutual enantiomer recognition in the radical recombination process.

UR - http://www.scopus.com/inward/record.url?scp=0028298610&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028298610&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)90447-8

DO - 10.1016/S0040-4020(01)90447-8

M3 - Article

AN - SCOPUS:0028298610

VL - 50

SP - 5927

EP - 5932

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 20

ER -