Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose

Liam R Cox; Gareth A DeBoos; Jeremy J Fullbrook; Jonathan Percy; Neil S Spencer; Malcolm Tolley

doi:10.1021/ol02735

Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose

Liam R Cox, Gareth A DeBoos, Jeremy J Fullbrook, Jonathan Percy, Neil S Spencer, Malcolm Tolley

Pure And Applied Chemistry

Research output: Contribution to journal › Article

32 Citations (Scopus)

Abstract

A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting groups were chosen to enhance the reactivity of the disubstituted allylic fragment in the AD reaction and allow deprotection under orthogonal conditions.

Original language	English
Pages (from-to)	337-339
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	3
DOIs	https://doi.org/10.1021/ol02735
Publication status	Published - 6 Feb 2003

Keywords

catalytic sysnthesis
Stille coupling
orthogonal conditions

Access to Document

10.1021/ol02735

Fingerprint Dive into the research topics of 'Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose'. Together they form a unique fingerprint.

Cite this

Cox, L. R., DeBoos, G. A., Fullbrook, J. J., Percy, J., Spencer, N. S., & Tolley, M. (2003). Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose. Organic Letters, 5(3), 337-339 . https://doi.org/10.1021/ol02735

@article{cbeb467f5d0e4330914ad23daa04ca31,

title = "Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose",

abstract = "A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting groups were chosen to enhance the reactivity of the disubstituted allylic fragment in the AD reaction and allow deprotection under orthogonal conditions. ",

keywords = "catalytic sysnthesis, Stille coupling, orthogonal conditions",

author = "Cox, {Liam R} and DeBoos, {Gareth A} and Fullbrook, {Jeremy J} and Jonathan Percy and Spencer, {Neil S} and Malcolm Tolley",

year = "2003",

month = feb,

day = "6",

doi = "10.1021/ol02735",

language = "English",

volume = "5",

pages = "337--339 ",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose

AU - Cox, Liam R

AU - DeBoos, Gareth A

AU - Fullbrook, Jeremy J

AU - Percy, Jonathan

AU - Spencer, Neil S

AU - Tolley, Malcolm

PY - 2003/2/6

Y1 - 2003/2/6

N2 - A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting groups were chosen to enhance the reactivity of the disubstituted allylic fragment in the AD reaction and allow deprotection under orthogonal conditions.

AB - A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting groups were chosen to enhance the reactivity of the disubstituted allylic fragment in the AD reaction and allow deprotection under orthogonal conditions.

KW - catalytic sysnthesis

KW - Stille coupling

KW - orthogonal conditions

U2 - 10.1021/ol02735

DO - 10.1021/ol02735

M3 - Article

VL - 5

SP - 337

EP - 339

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 3

ER -