Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

Osamu Kitagawa; Shu ichi Momose; Yoshihisa Fushimi; Takeo Taguchi

doi:10.1016/S0040-4039(99)01853-5

Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

Osamu Kitagawa, Shu ichi Momose, Yoshihisa Fushimi, Takeo Taguchi

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

57 Citations (Scopus)

Abstract

Various atropisomeric amides were prepared in optically pure forms (≥98% ee) through the optical resolution of the amide ester derived from (R)-pantolactone, N-allyl-ortho-tert-butylaniline and oxalyl chloride. Asymmetric carbonyl addition reaction of an alkyllithium and asymmetric iodolactonization with these atropisomeric amides proceeded with high stereoselectivity.

Original language	English
Pages (from-to)	8827-8831
Number of pages	5
Journal	Tetrahedron Letters
Volume	40
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4039(99)01853-5
Publication status	Published - 1999 Dec 10
Externally published	Yes

Keywords

Anilides
Asymmetric reaction
Atropisomerism
Resolution

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(99)01853-5

Cite this

@article{b855ef0bfbe54d6ba82df0f7652ad987,

title = "Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions",

abstract = "Various atropisomeric amides were prepared in optically pure forms (≥98% ee) through the optical resolution of the amide ester derived from (R)-pantolactone, N-allyl-ortho-tert-butylaniline and oxalyl chloride. Asymmetric carbonyl addition reaction of an alkyllithium and asymmetric iodolactonization with these atropisomeric amides proceeded with high stereoselectivity.",

keywords = "Anilides, Asymmetric reaction, Atropisomerism, Resolution",

author = "Osamu Kitagawa and Momose, {Shu ichi} and Yoshihisa Fushimi and Takeo Taguchi",

year = "1999",

month = dec,

day = "10",

doi = "10.1016/S0040-4039(99)01853-5",

language = "English",

volume = "40",

pages = "8827--8831",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "50",

}

TY - JOUR

T1 - Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

AU - Kitagawa, Osamu

AU - Momose, Shu ichi

AU - Fushimi, Yoshihisa

AU - Taguchi, Takeo

PY - 1999/12/10

Y1 - 1999/12/10

N2 - Various atropisomeric amides were prepared in optically pure forms (≥98% ee) through the optical resolution of the amide ester derived from (R)-pantolactone, N-allyl-ortho-tert-butylaniline and oxalyl chloride. Asymmetric carbonyl addition reaction of an alkyllithium and asymmetric iodolactonization with these atropisomeric amides proceeded with high stereoselectivity.

AB - Various atropisomeric amides were prepared in optically pure forms (≥98% ee) through the optical resolution of the amide ester derived from (R)-pantolactone, N-allyl-ortho-tert-butylaniline and oxalyl chloride. Asymmetric carbonyl addition reaction of an alkyllithium and asymmetric iodolactonization with these atropisomeric amides proceeded with high stereoselectivity.

KW - Anilides

KW - Asymmetric reaction

KW - Atropisomerism

KW - Resolution

UR - http://www.scopus.com/inward/record.url?scp=0033544759&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033544759&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)01853-5

DO - 10.1016/S0040-4039(99)01853-5

M3 - Article

AN - SCOPUS:0033544759

SN - 0040-4039

VL - 40

SP - 8827

EP - 8831

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this