Asymmetric Baylis-Hillman reactions using chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes catalysts under high pressure conditions

Tohru Oishi; Hiroki Oguri; Masahiro Hirama

doi:10.1016/0957-4166(95)00153-G

Asymmetric Baylis-Hillman reactions using chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes catalysts under high pressure conditions

Tohru Oishi, Hiroki Oguri, Masahiro Hirama

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

128 Citations (Scopus)

Abstract

Chiral C₂-symmetric 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes (DABCOs) (1) have been utilized as catalysts for asymmetric Baylis-Hillman reactions. Optically active α-methylene-β-hydroxyalkanone was obtained in up to 47% ee. Under high pressure conditions, a remarkable enhancement of both reaction rate and enantioselectivity has been observed.

Original language	English
Pages (from-to)	1241-1244
Number of pages	4
Journal	Tetrahedron: Asymmetry
Volume	6
Issue number	6
DOIs	https://doi.org/10.1016/0957-4166(95)00153-G
Publication status	Published - Jun 1995
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/0957-4166(95)00153-G

Cite this

@article{5ecc52bbfe854ce1893c1d8fabab77a3,

title = "Asymmetric Baylis-Hillman reactions using chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes catalysts under high pressure conditions",

abstract = "Chiral C2-symmetric 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes (DABCOs) (1) have been utilized as catalysts for asymmetric Baylis-Hillman reactions. Optically active α-methylene-β-hydroxyalkanone was obtained in up to 47% ee. Under high pressure conditions, a remarkable enhancement of both reaction rate and enantioselectivity has been observed.",

author = "Tohru Oishi and Hiroki Oguri and Masahiro Hirama",

year = "1995",

month = jun,

doi = "10.1016/0957-4166(95)00153-G",

language = "English",

volume = "6",

pages = "1241--1244",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "6",

}

TY - JOUR

T1 - Asymmetric Baylis-Hillman reactions using chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes catalysts under high pressure conditions

AU - Oishi, Tohru

AU - Oguri, Hiroki

AU - Hirama, Masahiro

PY - 1995/6

Y1 - 1995/6

N2 - Chiral C2-symmetric 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes (DABCOs) (1) have been utilized as catalysts for asymmetric Baylis-Hillman reactions. Optically active α-methylene-β-hydroxyalkanone was obtained in up to 47% ee. Under high pressure conditions, a remarkable enhancement of both reaction rate and enantioselectivity has been observed.

AB - Chiral C2-symmetric 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes (DABCOs) (1) have been utilized as catalysts for asymmetric Baylis-Hillman reactions. Optically active α-methylene-β-hydroxyalkanone was obtained in up to 47% ee. Under high pressure conditions, a remarkable enhancement of both reaction rate and enantioselectivity has been observed.

UR - http://www.scopus.com/inward/record.url?scp=0029078895&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029078895&partnerID=8YFLogxK

U2 - 10.1016/0957-4166(95)00153-G

DO - 10.1016/0957-4166(95)00153-G

M3 - Article

AN - SCOPUS:0029078895

SN - 0957-4166

VL - 6

SP - 1241

EP - 1244

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 6

ER -

Asymmetric Baylis-Hillman reactions using chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes catalysts under high pressure conditions

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this