Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates

Mitsuru Shindo; Soichiro Oya; Ryoko Murakami; Yusuke Sato; Kozo Shishido

doi:10.1016/S0040-4039(00)00986-2

Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates

Mitsuru Shindo, Soichiro Oya, Ryoko Murakami, Yusuke Sato, Kozo Shishido

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

26 Citations (Scopus)

Abstract

Lithium ynolates reacted with N-2-methoxyphenyl (OMP) aldimines to afford α,β-unsaturated amides in excellent E-selectivity via a retro- Mannich reaction of the 2:1 adducts (β-lactams), followed by cleavage of the β-lactam enolates. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	5947-5950
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(00)00986-2
Publication status	Published - Jul 29 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)00986-2

Cite this

@article{1e846334aa414fb29f28a5d7ad9719b3,

title = "Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates",

abstract = "Lithium ynolates reacted with N-2-methoxyphenyl (OMP) aldimines to afford α,β-unsaturated amides in excellent E-selectivity via a retro- Mannich reaction of the 2:1 adducts (β-lactams), followed by cleavage of the β-lactam enolates. (C) 2000 Elsevier Science Ltd.",

author = "Mitsuru Shindo and Soichiro Oya and Ryoko Murakami and Yusuke Sato and Kozo Shishido",

note = "Funding Information: This work was supported by Grants-in-Aid for Scientific Research on Priority Areas (No. 283, {\textquoteleft}Innovative Synthetic Reactions{\textquoteright}) from the Ministry of Education, Science, Sports and Culture, Government of Japan, and the Eisai Award in Synthetic Organic Chemistry, Japan.",

year = "2000",

month = jul,

day = "29",

doi = "10.1016/S0040-4039(00)00986-2",

language = "English",

volume = "41",

pages = "5947--5950",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "31",

}

TY - JOUR

T1 - Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates

AU - Shindo, Mitsuru

AU - Oya, Soichiro

AU - Murakami, Ryoko

AU - Sato, Yusuke

AU - Shishido, Kozo

N1 - Funding Information: This work was supported by Grants-in-Aid for Scientific Research on Priority Areas (No. 283, ‘Innovative Synthetic Reactions’) from the Ministry of Education, Science, Sports and Culture, Government of Japan, and the Eisai Award in Synthetic Organic Chemistry, Japan.

PY - 2000/7/29

Y1 - 2000/7/29

N2 - Lithium ynolates reacted with N-2-methoxyphenyl (OMP) aldimines to afford α,β-unsaturated amides in excellent E-selectivity via a retro- Mannich reaction of the 2:1 adducts (β-lactams), followed by cleavage of the β-lactam enolates. (C) 2000 Elsevier Science Ltd.

AB - Lithium ynolates reacted with N-2-methoxyphenyl (OMP) aldimines to afford α,β-unsaturated amides in excellent E-selectivity via a retro- Mannich reaction of the 2:1 adducts (β-lactams), followed by cleavage of the β-lactam enolates. (C) 2000 Elsevier Science Ltd.

UR - http://www.scopus.com/inward/record.url?scp=0034730009&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034730009&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)00986-2

DO - 10.1016/S0040-4039(00)00986-2

M3 - Article

AN - SCOPUS:0034730009

VL - 41

SP - 5947

EP - 5950

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 31

ER -

Highly E-selective synthesis of α,β-unsaturated amides from N-2- methoxyphenyl aldimines via lithium ynolates

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this