Asymmetric autocatalysis of 5-carbamoyl-3-pyridyl alkanols with amplification of enantiomeric excess

Shigehisa Tanji; Yasutaka Kodaka; Atsushi Ohno; Takanori Shibata; Itaru Sato; Kenso Soai

doi:10.1016/S0957-4166(00)00420-1

Asymmetric autocatalysis of 5-carbamoyl-3-pyridyl alkanols with amplification of enantiomeric excess

Shigehisa Tanji, Yasutaka Kodaka, Atsushi Ohno, Takanori Shibata, Itaru Sato, Kenso Soai^*

^*Corresponding author for this work

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

37 Citations (Scopus)

Abstract

5-Carbamoyl-3-pyridyl alkanols with low e.e. act as asymmetric autocatalysts in the consecutive asymmetric autocatalytic addition of diisopropylzinc to 5-carbamoyl-3-pyridinecarbaldehydes. The e.e. of pyridyl alkanol amplified up to 88% e.e. without the need for any other chiral auxiliary. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	4249-4253
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	11
Issue number	21
DOIs	https://doi.org/10.1016/S0957-4166(00)00420-1
Publication status	Published - 2000 Nov 3
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/S0957-4166(00)00420-1

Cite this

@article{da7e710abc424db98c767538fdd87b05,

title = "Asymmetric autocatalysis of 5-carbamoyl-3-pyridyl alkanols with amplification of enantiomeric excess",

abstract = "5-Carbamoyl-3-pyridyl alkanols with low e.e. act as asymmetric autocatalysts in the consecutive asymmetric autocatalytic addition of diisopropylzinc to 5-carbamoyl-3-pyridinecarbaldehydes. The e.e. of pyridyl alkanol amplified up to 88% e.e. without the need for any other chiral auxiliary. (C) 2000 Elsevier Science Ltd.",

author = "Shigehisa Tanji and Yasutaka Kodaka and Atsushi Ohno and Takanori Shibata and Itaru Sato and Kenso Soai",

note = "Funding Information: Financial support from the Ministry of Education, Science, Sports and Culture and Japan Space Forum is gratefully acknowledged. We thank Ms Harumi Aiyagi for technical assistance.",

year = "2000",

month = nov,

day = "3",

doi = "10.1016/S0957-4166(00)00420-1",

language = "English",

volume = "11",

pages = "4249--4253",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "21",

}

TY - JOUR

T1 - Asymmetric autocatalysis of 5-carbamoyl-3-pyridyl alkanols with amplification of enantiomeric excess

AU - Tanji, Shigehisa

AU - Kodaka, Yasutaka

AU - Ohno, Atsushi

AU - Shibata, Takanori

AU - Sato, Itaru

AU - Soai, Kenso

N1 - Funding Information: Financial support from the Ministry of Education, Science, Sports and Culture and Japan Space Forum is gratefully acknowledged. We thank Ms Harumi Aiyagi for technical assistance.

PY - 2000/11/3

Y1 - 2000/11/3

N2 - 5-Carbamoyl-3-pyridyl alkanols with low e.e. act as asymmetric autocatalysts in the consecutive asymmetric autocatalytic addition of diisopropylzinc to 5-carbamoyl-3-pyridinecarbaldehydes. The e.e. of pyridyl alkanol amplified up to 88% e.e. without the need for any other chiral auxiliary. (C) 2000 Elsevier Science Ltd.

AB - 5-Carbamoyl-3-pyridyl alkanols with low e.e. act as asymmetric autocatalysts in the consecutive asymmetric autocatalytic addition of diisopropylzinc to 5-carbamoyl-3-pyridinecarbaldehydes. The e.e. of pyridyl alkanol amplified up to 88% e.e. without the need for any other chiral auxiliary. (C) 2000 Elsevier Science Ltd.

UR - http://www.scopus.com/inward/record.url?scp=0034601960&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034601960&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(00)00420-1

DO - 10.1016/S0957-4166(00)00420-1

M3 - Article

AN - SCOPUS:0034601960

SN - 0957-4166

VL - 11

SP - 4249

EP - 4253

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 21

ER -

Asymmetric autocatalysis of 5-carbamoyl-3-pyridyl alkanols with amplification of enantiomeric excess

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this