Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides

Osamu Kitagawa; Shu Ichi Momose; Yoichiro Yamada; Motoo Shiro; Takeo Taguchi

doi:10.1016/S0040-4039(01)00868-1

Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides

Osamu Kitagawa, Shu Ichi Momose, Yoichiro Yamada, Motoo Shiro, Takeo Taguchi

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

Treatment of chiral α-benzyloxy- or α-propargyloxycarboxamide with tert-BuLi gave β-hydroxycarboxamides (aldol derivatives) in high optical purity through the formation of α-lithiated ethers and the subsquent 1,2-Wittig rearrangement.

Original language	English
Pages (from-to)	4865-4868
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4039(01)00868-1
Publication status	Published - 2001 Jul 16
Externally published	Yes

Keywords

Aldols
Asymmetric reaction
Hydroxy acids and derivatives
Wittig rearrangement

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(01)00868-1

Cite this

@article{57a6e33e66874cfb80f252bf8dfda1b6,

title = "Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides",

abstract = "Treatment of chiral α-benzyloxy- or α-propargyloxycarboxamide with tert-BuLi gave β-hydroxycarboxamides (aldol derivatives) in high optical purity through the formation of α-lithiated ethers and the subsquent 1,2-Wittig rearrangement.",

keywords = "Aldols, Asymmetric reaction, Hydroxy acids and derivatives, Wittig rearrangement",

author = "Osamu Kitagawa and Momose, {Shu Ichi} and Yoichiro Yamada and Motoo Shiro and Takeo Taguchi",

year = "2001",

month = jul,

day = "16",

doi = "10.1016/S0040-4039(01)00868-1",

language = "English",

volume = "42",

pages = "4865--4868",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "29",

}

TY - JOUR

T1 - Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides

AU - Kitagawa, Osamu

AU - Momose, Shu Ichi

AU - Yamada, Yoichiro

AU - Shiro, Motoo

AU - Taguchi, Takeo

PY - 2001/7/16

Y1 - 2001/7/16

N2 - Treatment of chiral α-benzyloxy- or α-propargyloxycarboxamide with tert-BuLi gave β-hydroxycarboxamides (aldol derivatives) in high optical purity through the formation of α-lithiated ethers and the subsquent 1,2-Wittig rearrangement.

AB - Treatment of chiral α-benzyloxy- or α-propargyloxycarboxamide with tert-BuLi gave β-hydroxycarboxamides (aldol derivatives) in high optical purity through the formation of α-lithiated ethers and the subsquent 1,2-Wittig rearrangement.

KW - Aldols

KW - Asymmetric reaction

KW - Hydroxy acids and derivatives

KW - Wittig rearrangement

UR - http://www.scopus.com/inward/record.url?scp=0035898835&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035898835&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)00868-1

DO - 10.1016/S0040-4039(01)00868-1

M3 - Article

AN - SCOPUS:0035898835

SN - 0040-4039

VL - 42

SP - 4865

EP - 4868

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this