Gold-catalyzed highly enantioselective synthesis of axially chiral allenes

Vanessa Kar Yan Lo; Man Kin Wong; Chi Ming Che

doi:10.1021/ol702970r

Gold-catalyzed highly enantioselective synthesis of axially chiral allenes

Vanessa Kar Yan Lo, Man Kin Wong, Chi Ming Che

Research output: Journal article publication › Journal article › Academic research › peer-review

135 Citations (Scopus)

Abstract

Axially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthesis of novel allene-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. A tentative mechanism regarding gold(l)-catalyzed intramolecular hydride transfer was proposed on the basis of deuterium-labeling experiments and ESI-MS analysis of the reaction mixture.

Original language	English
Pages (from-to)	517-519
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	3
DOIs	https://doi.org/10.1021/ol702970r
Publication status	Published - 7 Feb 2008
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

More information

10.1021/ol702970r

Cite this

@article{5be6d27b30484bfa934123cac7cef0ac,

title = "Gold-catalyzed highly enantioselective synthesis of axially chiral allenes",

abstract = "Axially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthesis of novel allene-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. A tentative mechanism regarding gold(l)-catalyzed intramolecular hydride transfer was proposed on the basis of deuterium-labeling experiments and ESI-MS analysis of the reaction mixture.",

author = "Lo, {Vanessa Kar Yan} and Wong, {Man Kin} and Che, {Chi Ming}",

year = "2008",

month = feb,

day = "7",

doi = "10.1021/ol702970r",

language = "English",

volume = "10",

pages = "517--519",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Gold-catalyzed highly enantioselective synthesis of axially chiral allenes

AU - Lo, Vanessa Kar Yan

AU - Wong, Man Kin

AU - Che, Chi Ming

PY - 2008/2/7

Y1 - 2008/2/7

N2 - Axially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthesis of novel allene-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. A tentative mechanism regarding gold(l)-catalyzed intramolecular hydride transfer was proposed on the basis of deuterium-labeling experiments and ESI-MS analysis of the reaction mixture.

AB - Axially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthesis of novel allene-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. A tentative mechanism regarding gold(l)-catalyzed intramolecular hydride transfer was proposed on the basis of deuterium-labeling experiments and ESI-MS analysis of the reaction mixture.

UR - http://www.scopus.com/inward/record.url?scp=38949112395&partnerID=8YFLogxK

U2 - 10.1021/ol702970r

DO - 10.1021/ol702970r

M3 - Journal article

C2 - 18181641

SN - 1523-7060

VL - 10

SP - 517

EP - 519

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Gold-catalyzed highly enantioselective synthesis of axially chiral allenes

Abstract

ASJC Scopus subject areas

More information

Other files and links

Fingerprint

Cite this