Isothiourea-Catalyzed Asymmetric O- to C-Carboxyl Transfer of Furanyl Carbonates

Caroline Joannesse; Louis C. Morrill; Craig D. Campbell; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1055/s-0030-1260602

Isothiourea-Catalyzed Asymmetric O- to C-Carboxyl Transfer of Furanyl Carbonates

Caroline Joannesse
, Louis C. Morrill
, Craig D. Campbell
, Alexandra M. Z. Slawin
, Andrew D. Smith

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

Abstract

The ability of a chiral isothiourea to promote the regio- and enantioselective O- to C-carboxyl transfer of a series of 3-alkyl-5-aryl- and 5-methyl-3-phenylfuranyl carbonates is examined, generating preferentially the alpha-regioisomers (alpha/gamma up to 83:17) with high asymmetric induction (up to 83% ee).

Original language	English
Pages (from-to)	1865-1879
Number of pages	15
Journal	Synthesis
Issue number	12
DOIs	https://doi.org/10.1055/s-0030-1260602
Publication status	Published - Jun 2011

Keywords

isothiourea
organocatalysis
carboxyl transfer
furanyl carbonates
butenolides
ACYL-TRANSFER CATALYST
SECONDARY BENZYLIC ALCOHOLS
STEGLICH REARRANGEMENT REACTION
EFFECTIVE KINETIC RESOLUTION
ENANTIOSELECTIVE SYNTHESIS
TETRAMISOLE DERIVATIVES
NUCLEOPHILIC CATALYSTS
BENZOIC ANHYDRIDES
PIVALIC ANHYDRIDE
QUATERNARY CARBON

Access to Document

10.1055/s-0030-1260602

Handle.net

Persistent link to portal record

Cite this

@article{bfb75fb321834dea81dba34e26cdfd83,

title = "Isothiourea-Catalyzed Asymmetric O- to C-Carboxyl Transfer of Furanyl Carbonates",

abstract = "The ability of a chiral isothiourea to promote the regio- and enantioselective O- to C-carboxyl transfer of a series of 3-alkyl-5-aryl- and 5-methyl-3-phenylfuranyl carbonates is examined, generating preferentially the alpha-regioisomers (alpha/gamma up to 83:17) with high asymmetric induction (up to 83\% ee).",

keywords = "isothiourea, organocatalysis, carboxyl transfer, furanyl carbonates, butenolides, ACYL-TRANSFER CATALYST, SECONDARY BENZYLIC ALCOHOLS, STEGLICH REARRANGEMENT REACTION, EFFECTIVE KINETIC RESOLUTION, ENANTIOSELECTIVE SYNTHESIS, TETRAMISOLE DERIVATIVES, NUCLEOPHILIC CATALYSTS, BENZOIC ANHYDRIDES, PIVALIC ANHYDRIDE, QUATERNARY CARBON",

author = "Caroline Joannesse and Morrill, \{Louis C.\} and Campbell, \{Craig D.\} and Slawin, \{Alexandra M. Z.\} and Smith, \{Andrew D.\}",

year = "2011",

month = jun,

doi = "10.1055/s-0030-1260602",

language = "English",

pages = "1865--1879",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "12",

}

TY - JOUR

T1 - Isothiourea-Catalyzed Asymmetric O- to C-Carboxyl Transfer of Furanyl Carbonates

AU - Joannesse, Caroline

AU - Morrill, Louis C.

AU - Campbell, Craig D.

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

PY - 2011/6

Y1 - 2011/6

N2 - The ability of a chiral isothiourea to promote the regio- and enantioselective O- to C-carboxyl transfer of a series of 3-alkyl-5-aryl- and 5-methyl-3-phenylfuranyl carbonates is examined, generating preferentially the alpha-regioisomers (alpha/gamma up to 83:17) with high asymmetric induction (up to 83% ee).

AB - The ability of a chiral isothiourea to promote the regio- and enantioselective O- to C-carboxyl transfer of a series of 3-alkyl-5-aryl- and 5-methyl-3-phenylfuranyl carbonates is examined, generating preferentially the alpha-regioisomers (alpha/gamma up to 83:17) with high asymmetric induction (up to 83% ee).

KW - isothiourea

KW - organocatalysis

KW - carboxyl transfer

KW - furanyl carbonates

KW - butenolides

KW - ACYL-TRANSFER CATALYST

KW - SECONDARY BENZYLIC ALCOHOLS

KW - STEGLICH REARRANGEMENT REACTION

KW - EFFECTIVE KINETIC RESOLUTION

KW - ENANTIOSELECTIVE SYNTHESIS

KW - TETRAMISOLE DERIVATIVES

KW - NUCLEOPHILIC CATALYSTS

KW - BENZOIC ANHYDRIDES

KW - PIVALIC ANHYDRIDE

KW - QUATERNARY CARBON

U2 - 10.1055/s-0030-1260602

DO - 10.1055/s-0030-1260602

M3 - Article

SN - 0039-7881

SP - 1865

EP - 1879

JO - Synthesis

JF - Synthesis

IS - 12

ER -