Isothiourea-Mediated Stereoselective C-Acylation of Silyl Ketene Acetals

Philip A. Woods; Louis C. Morrill; Tomas Lebl; Alexandra M. Z. Slawin; Ryan A. Bragg; Andrew D. Smith

doi:10.1021/ol1008747

Isothiourea-Mediated Stereoselective C-Acylation of Silyl Ketene Acetals

Philip A. Woods, Louis C. Morrill, Tomas Lebl, Alexandra M. Z. Slawin, Ryan A. Bragg, Andrew D. Smith

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

42 Citations (Scopus)

Abstract

Isothiourea DHPB promotes the diastereoselective C-acylation of silyl ketene acetals with anhydrides or benzoyl fluoride, giving 3-acy1-3-aryl or 3-acyl-3-alkylfuranones in excellent yields and stereoselectivities (up to 99:1 dr).

Original language	English
Pages (from-to)	2660-2663
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	11
DOIs	https://doi.org/10.1021/ol1008747
Publication status	Published - 4 Jun 2010

Keywords

BETA,BETA-DISUBSTITUTED GAMMA-BUTYROLACTONES
CATALYTIC ENANTIOSELECTIVE SYNTHESIS
CARBON QUATERNARY STEREOCENTERS
ASYMMETRIC-SYNTHESIS
1,3-DICARBONYL COMPOUNDS
METHYL CYANOFORMATE
BETA-KETOESTERS
ACYL TRANSFER
O-CARBOXYL
CONSTRUCTION

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title = "Isothiourea-Mediated Stereoselective C-Acylation of Silyl Ketene Acetals",

abstract = "Isothiourea DHPB promotes the diastereoselective C-acylation of silyl ketene acetals with anhydrides or benzoyl fluoride, giving 3-acy1-3-aryl or 3-acyl-3-alkylfuranones in excellent yields and stereoselectivities (up to 99:1 dr).",

keywords = "BETA,BETA-DISUBSTITUTED GAMMA-BUTYROLACTONES, CATALYTIC ENANTIOSELECTIVE SYNTHESIS, CARBON QUATERNARY STEREOCENTERS, ASYMMETRIC-SYNTHESIS, 1,3-DICARBONYL COMPOUNDS, METHYL CYANOFORMATE, BETA-KETOESTERS, ACYL TRANSFER, O-CARBOXYL, CONSTRUCTION",

author = "Woods, {Philip A.} and Morrill, {Louis C.} and Tomas Lebl and Slawin, {Alexandra M. Z.} and Bragg, {Ryan A.} and Smith, {Andrew D.}",

year = "2010",

month = jun,

day = "4",

doi = "10.1021/ol1008747",

language = "English",

volume = "12",

pages = "2660--2663",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "11",

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TY - JOUR

T1 - Isothiourea-Mediated Stereoselective C-Acylation of Silyl Ketene Acetals

AU - Woods, Philip A.

AU - Morrill, Louis C.

AU - Lebl, Tomas

AU - Slawin, Alexandra M. Z.

AU - Bragg, Ryan A.

AU - Smith, Andrew D.

PY - 2010/6/4

Y1 - 2010/6/4

N2 - Isothiourea DHPB promotes the diastereoselective C-acylation of silyl ketene acetals with anhydrides or benzoyl fluoride, giving 3-acy1-3-aryl or 3-acyl-3-alkylfuranones in excellent yields and stereoselectivities (up to 99:1 dr).

AB - Isothiourea DHPB promotes the diastereoselective C-acylation of silyl ketene acetals with anhydrides or benzoyl fluoride, giving 3-acy1-3-aryl or 3-acyl-3-alkylfuranones in excellent yields and stereoselectivities (up to 99:1 dr).

KW - BETA,BETA-DISUBSTITUTED GAMMA-BUTYROLACTONES

KW - CATALYTIC ENANTIOSELECTIVE SYNTHESIS

KW - CARBON QUATERNARY STEREOCENTERS

KW - ASYMMETRIC-SYNTHESIS

KW - 1,3-DICARBONYL COMPOUNDS

KW - METHYL CYANOFORMATE

KW - BETA-KETOESTERS

KW - ACYL TRANSFER

KW - O-CARBOXYL

KW - CONSTRUCTION

U2 - 10.1021/ol1008747

DO - 10.1021/ol1008747

M3 - Article

SN - 1523-7060

VL - 12

SP - 2660

EP - 2663

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Isothiourea-Mediated Stereoselective C-Acylation of Silyl Ketene Acetals

Abstract

Keywords

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