Enantiopure guanidine bases for enantioselective enone epoxidations: 1, acyclic guanidines

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

Enantiopure guanidine bases for enantioselective enone epoxidations: 1, acyclic guanidines

J C McManus, 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 guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tert-butoxycarbonylamino-4,4dimethoxycyclohexa-2,5-dien- 1-one 1 using tert-butylhydroperoxide. Successful enantioselective epoxidations were observed and useful structure-activity data obtained, but the reactions were slow and the maximum ee observed was 30%.

Original language	English
Pages (from-to)	365-368
Number of pages	4
Journal	Synlett
Issue number	3
Publication status	Published - Feb 2003

Keywords

enantioselective
epoxidation
enones
guanidines
stereo selectivity
MANUMYCIN-A
ANALOGS
CONVENIENT
ROUTE

Cite this

@article{6b21f57d751442868b1453285ee45808,

title = "Enantiopure guanidine bases for enantioselective enone epoxidations: 1, acyclic guanidines",

abstract = "A range of structurally and functionally varied enantiopure guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tert-butoxycarbonylamino-4,4dimethoxycyclohexa-2,5-dien- 1-one 1 using tert-butylhydroperoxide. Successful enantioselective epoxidations were observed and useful structure-activity data obtained, but the reactions were slow and the maximum ee observed was 30%.",

keywords = "enantioselective, epoxidation, enones, guanidines, stereo selectivity, MANUMYCIN-A, ANALOGS, CONVENIENT, ROUTE",

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

year = "2003",

month = feb,

language = "English",

pages = "365--368",

journal = "Synlett",

issn = "1437-2096",

publisher = "Georg Thieme Verlag",

number = "3",

}

TY - JOUR

T1 - Enantiopure guanidine bases for enantioselective enone epoxidations: 1, acyclic guanidines

AU - McManus, J C

AU - Carey, J S

AU - Taylor, R J K

PY - 2003/2

Y1 - 2003/2

N2 - A range of structurally and functionally varied enantiopure guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tert-butoxycarbonylamino-4,4dimethoxycyclohexa-2,5-dien- 1-one 1 using tert-butylhydroperoxide. Successful enantioselective epoxidations were observed and useful structure-activity data obtained, but the reactions were slow and the maximum ee observed was 30%.

AB - A range of structurally and functionally varied enantiopure guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tert-butoxycarbonylamino-4,4dimethoxycyclohexa-2,5-dien- 1-one 1 using tert-butylhydroperoxide. Successful enantioselective epoxidations were observed and useful structure-activity data obtained, but the reactions were slow and the maximum ee observed was 30%.

KW - enantioselective

KW - epoxidation

KW - enones

KW - guanidines

KW - stereo selectivity

KW - MANUMYCIN-A

KW - ANALOGS

KW - CONVENIENT

KW - ROUTE

M3 - Article

SN - 1437-2096

SP - 365

EP - 368

JO - Synlett

JF - Synlett

IS - 3

ER -