Enantiopure guanidine bases for enantioselective enone epoxidations: 2, cyclic guanidines

J C  McManus; T  Genski; J S  Carey; R J K  Taylor

Enantiopure guanidine bases for enantioselective enone epoxidations: 2, cyclic guanidines

J C McManus, T Genski, J S Carey, R J K Taylor

Chemistry

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

Abstract

A range of structurally and functionally varied enantiopure cyclic and bicyclic guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tertbutoxycarbonylamino-4,4-dimethoxycyclohexa-2,5-dien- 1-one 1 using tert-butylhydroperoxide. Encouraging enantiomeric excesses were observed (up to 60%). Low enantiomeric excesses were also observed with 2-methylnaphthoquinone and trans-chalcone.

Original language	English
Pages (from-to)	369-371
Number of pages	3
Journal	Synlett
Issue number	3
Publication status	Published - Feb 2003

Keywords

enantioselective
epoxidation
enones
guanidines
stereo selectivity

Cite this

@article{3ab483db807547fa89f2532bd77ee1e2,

title = "Enantiopure guanidine bases for enantioselective enone epoxidations: 2, cyclic guanidines",

abstract = "A range of structurally and functionally varied enantiopure cyclic and bicyclic guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tertbutoxycarbonylamino-4,4-dimethoxycyclohexa-2,5-dien- 1-one 1 using tert-butylhydroperoxide. Encouraging enantiomeric excesses were observed (up to 60%). Low enantiomeric excesses were also observed with 2-methylnaphthoquinone and trans-chalcone.",

keywords = "enantioselective, epoxidation, enones, guanidines, stereo selectivity",

author = "McManus, {J C} and T Genski and Carey, {J S} and Taylor, {R J K}",

year = "2003",

month = feb,

language = "English",

pages = "369--371",

journal = "Synlett",

issn = "1437-2096",

publisher = "Georg Thieme Verlag",

number = "3",

}

TY - JOUR

T1 - Enantiopure guanidine bases for enantioselective enone epoxidations: 2, cyclic guanidines

AU - McManus, J C

AU - Genski, T

AU - Carey, J S

AU - Taylor, R J K

PY - 2003/2

Y1 - 2003/2

N2 - A range of structurally and functionally varied enantiopure cyclic and bicyclic guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tertbutoxycarbonylamino-4,4-dimethoxycyclohexa-2,5-dien- 1-one 1 using tert-butylhydroperoxide. Encouraging enantiomeric excesses were observed (up to 60%). Low enantiomeric excesses were also observed with 2-methylnaphthoquinone and trans-chalcone.

AB - A range of structurally and functionally varied enantiopure cyclic and bicyclic guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tertbutoxycarbonylamino-4,4-dimethoxycyclohexa-2,5-dien- 1-one 1 using tert-butylhydroperoxide. Encouraging enantiomeric excesses were observed (up to 60%). Low enantiomeric excesses were also observed with 2-methylnaphthoquinone and trans-chalcone.

KW - enantioselective

KW - epoxidation

KW - enones

KW - guanidines

KW - stereo selectivity

M3 - Article

SN - 1437-2096

SP - 369

EP - 371

JO - Synlett

JF - Synlett

IS - 3

ER -