Asymmetric synthesis of various chiral 5-pyrimidyl-alkanols by the enantios elective alkylation of pyrimidine-5-carbaldehydes with dialkylzincs in the presence of chiral amino alcohols

Takanori Shibata, Tadakatsu Hayase, Yasuyuki Aiba, Hayami Tabira, Kenso Soai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

(1S,2R)-N,N-Dibutylnorephedrine catalyzes the enantioselective addition of dialkylzincs to various pyrimidine-5-carbaldehydes. Ethylation and butylation proceed with high enantioselectivities (up to 94% e.e.) to give optically active secondary 5-pyrimidyl alkanols.

Original languageEnglish
Pages (from-to)235-240
Number of pages6
JournalHeterocycles
Volume46
Issue number1
Publication statusPublished - 1997
Externally publishedYes

Fingerprint

Amino Alcohols
Enantioselectivity
Alkylation
pyrimidine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Asymmetric synthesis of various chiral 5-pyrimidyl-alkanols by the enantios elective alkylation of pyrimidine-5-carbaldehydes with dialkylzincs in the presence of chiral amino alcohols. / Shibata, Takanori; Hayase, Tadakatsu; Aiba, Yasuyuki; Tabira, Hayami; Soai, Kenso.

In: Heterocycles, Vol. 46, No. 1, 1997, p. 235-240.

Research output: Contribution to journalArticle

@article{74471eca9dd74e079b64d55038a17017,
title = "Asymmetric synthesis of various chiral 5-pyrimidyl-alkanols by the enantios elective alkylation of pyrimidine-5-carbaldehydes with dialkylzincs in the presence of chiral amino alcohols",
abstract = "(1S,2R)-N,N-Dibutylnorephedrine catalyzes the enantioselective addition of dialkylzincs to various pyrimidine-5-carbaldehydes. Ethylation and butylation proceed with high enantioselectivities (up to 94{\%} e.e.) to give optically active secondary 5-pyrimidyl alkanols.",
author = "Takanori Shibata and Tadakatsu Hayase and Yasuyuki Aiba and Hayami Tabira and Kenso Soai",
year = "1997",
language = "English",
volume = "46",
pages = "235--240",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "1",

}

TY - JOUR

T1 - Asymmetric synthesis of various chiral 5-pyrimidyl-alkanols by the enantios elective alkylation of pyrimidine-5-carbaldehydes with dialkylzincs in the presence of chiral amino alcohols

AU - Shibata, Takanori

AU - Hayase, Tadakatsu

AU - Aiba, Yasuyuki

AU - Tabira, Hayami

AU - Soai, Kenso

PY - 1997

Y1 - 1997

N2 - (1S,2R)-N,N-Dibutylnorephedrine catalyzes the enantioselective addition of dialkylzincs to various pyrimidine-5-carbaldehydes. Ethylation and butylation proceed with high enantioselectivities (up to 94% e.e.) to give optically active secondary 5-pyrimidyl alkanols.

AB - (1S,2R)-N,N-Dibutylnorephedrine catalyzes the enantioselective addition of dialkylzincs to various pyrimidine-5-carbaldehydes. Ethylation and butylation proceed with high enantioselectivities (up to 94% e.e.) to give optically active secondary 5-pyrimidyl alkanols.

UR - http://www.scopus.com/inward/record.url?scp=0011662607&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0011662607&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0011662607

VL - 46

SP - 235

EP - 240

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 1

ER -