External chiral ligand-induced enantioselective versions of the [2,3]- Wittig sigmatropic rearrangement

Katsuhiko Tomooka, Nobuyuki Komine, Takeshi Nakai

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The external chiral ligand-induced enantioselective [2,3]-Wittig rearrangements of crotyl benzyl ethers and crotyl propargylic ethers are described. The most notable is that treatment of (E)-crotyl propargylic ethers with a t-butyllithium/(S;S)-bis (oxazoline) complex provides a relatively high enantioselectivity (up to 89% ee), together with a high threo-diastereoselectivity. Furthermore, examples of the 'asymmetric catalytic version' of the rearrangement of crotyl benzyl ethers are presented. (C) 2000 Wiley-Liss, Inc.

Original languageEnglish
Pages (from-to)505-509
Number of pages5
JournalChirality
Volume12
Issue number5-6
Publication statusPublished - 2000
Externally publishedYes

Fingerprint

Ethers
Ligands
Enantioselectivity

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

External chiral ligand-induced enantioselective versions of the [2,3]- Wittig sigmatropic rearrangement. / Tomooka, Katsuhiko; Komine, Nobuyuki; Nakai, Takeshi.

In: Chirality, Vol. 12, No. 5-6, 2000, p. 505-509.

Research output: Contribution to journalArticle

@article{6a130e0211d84938a8af542d57a4e36a,
title = "External chiral ligand-induced enantioselective versions of the [2,3]- Wittig sigmatropic rearrangement",
abstract = "The external chiral ligand-induced enantioselective [2,3]-Wittig rearrangements of crotyl benzyl ethers and crotyl propargylic ethers are described. The most notable is that treatment of (E)-crotyl propargylic ethers with a t-butyllithium/(S;S)-bis (oxazoline) complex provides a relatively high enantioselectivity (up to 89{\%} ee), together with a high threo-diastereoselectivity. Furthermore, examples of the 'asymmetric catalytic version' of the rearrangement of crotyl benzyl ethers are presented. (C) 2000 Wiley-Liss, Inc.",
author = "Katsuhiko Tomooka and Nobuyuki Komine and Takeshi Nakai",
year = "2000",
language = "English",
volume = "12",
pages = "505--509",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "5-6",

}

TY - JOUR

T1 - External chiral ligand-induced enantioselective versions of the [2,3]- Wittig sigmatropic rearrangement

AU - Tomooka, Katsuhiko

AU - Komine, Nobuyuki

AU - Nakai, Takeshi

PY - 2000

Y1 - 2000

N2 - The external chiral ligand-induced enantioselective [2,3]-Wittig rearrangements of crotyl benzyl ethers and crotyl propargylic ethers are described. The most notable is that treatment of (E)-crotyl propargylic ethers with a t-butyllithium/(S;S)-bis (oxazoline) complex provides a relatively high enantioselectivity (up to 89% ee), together with a high threo-diastereoselectivity. Furthermore, examples of the 'asymmetric catalytic version' of the rearrangement of crotyl benzyl ethers are presented. (C) 2000 Wiley-Liss, Inc.

AB - The external chiral ligand-induced enantioselective [2,3]-Wittig rearrangements of crotyl benzyl ethers and crotyl propargylic ethers are described. The most notable is that treatment of (E)-crotyl propargylic ethers with a t-butyllithium/(S;S)-bis (oxazoline) complex provides a relatively high enantioselectivity (up to 89% ee), together with a high threo-diastereoselectivity. Furthermore, examples of the 'asymmetric catalytic version' of the rearrangement of crotyl benzyl ethers are presented. (C) 2000 Wiley-Liss, Inc.

UR - http://www.scopus.com/inward/record.url?scp=0034085190&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034085190&partnerID=8YFLogxK

M3 - Article

C2 - 10824178

AN - SCOPUS:0034085190

VL - 12

SP - 505

EP - 509

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 5-6

ER -