Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (+/-)-N-benzyl-coerulescine and (+/-)-horsfiline

Jennifer E. Thomson; Andrew F. Kyle; Kenneth B. Ling; Siobhan R. Smith; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1016/j.tet.2010.03.047

Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (+/-)-N-benzyl-coerulescine and (+/-)-horsfiline

Jennifer E. Thomson, Andrew F. Kyle, Kenneth B. Ling, Siobhan R. Smith, Alexandra M. Z. Slawin, Andrew D. Smith

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

Abstract

NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (+/-)-N-benzylcoerulescine and (+/-)-horsfiline. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3801-3813
Number of pages	13
Journal	Tetrahedron
Volume	66
Issue number	21
DOIs	https://doi.org/10.1016/j.tet.2010.03.047
Publication status	Published - 22 May 2010

Keywords

Lewis-base catalysis
N-heterocyclic carbene
Organocatalysis
Carboxyl transfer
Spiro[pyrrolidine-3,3 '-oxindole]
N-HETEROCYCLIC CARBENE
HIGHLY ENANTIOSELECTIVE SYNTHESIS
MAMMALIAN-CELL CYCLE
OXINDOLE ALKALOIDS
PROCHIRAL NUCLEOPHILES
DISUBSTITUTED KETENES
ASPERGILLUS-FUMIGATUS
ASYMMETRIC-SYNTHESIS
SPIROTRYPROSTATIN-B
RADICAL CYCLIZATION

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@article{5970aaa5220e484f9551cd09a3d9ab8f,

title = "Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (+/-)-N-benzyl-coerulescine and (+/-)-horsfiline",

abstract = "NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (+/-)-N-benzylcoerulescine and (+/-)-horsfiline. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "Lewis-base catalysis, N-heterocyclic carbene, Organocatalysis, Carboxyl transfer, Spiro[pyrrolidine-3,3 '-oxindole], N-HETEROCYCLIC CARBENE, HIGHLY ENANTIOSELECTIVE SYNTHESIS, MAMMALIAN-CELL CYCLE, OXINDOLE ALKALOIDS, PROCHIRAL NUCLEOPHILES, DISUBSTITUTED KETENES, ASPERGILLUS-FUMIGATUS, ASYMMETRIC-SYNTHESIS, SPIROTRYPROSTATIN-B, RADICAL CYCLIZATION",

author = "Thomson, {Jennifer E.} and Kyle, {Andrew F.} and Ling, {Kenneth B.} and Smith, {Siobhan R.} and Slawin, {Alexandra M. Z.} and Smith, {Andrew D.}",

year = "2010",

month = may,

day = "22",

doi = "10.1016/j.tet.2010.03.047",

language = "English",

volume = "66",

pages = "3801--3813",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "21",

}

TY - JOUR

T1 - Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (+/-)-N-benzyl-coerulescine and (+/-)-horsfiline

AU - Thomson, Jennifer E.

AU - Kyle, Andrew F.

AU - Ling, Kenneth B.

AU - Smith, Siobhan R.

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

PY - 2010/5/22

Y1 - 2010/5/22

N2 - NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (+/-)-N-benzylcoerulescine and (+/-)-horsfiline. (C) 2010 Elsevier Ltd. All rights reserved.

AB - NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (+/-)-N-benzylcoerulescine and (+/-)-horsfiline. (C) 2010 Elsevier Ltd. All rights reserved.

KW - Lewis-base catalysis

KW - N-heterocyclic carbene

KW - Organocatalysis

KW - Carboxyl transfer

KW - Spiro[pyrrolidine-3,3 '-oxindole]

KW - N-HETEROCYCLIC CARBENE

KW - HIGHLY ENANTIOSELECTIVE SYNTHESIS

KW - MAMMALIAN-CELL CYCLE

KW - OXINDOLE ALKALOIDS

KW - PROCHIRAL NUCLEOPHILES

KW - DISUBSTITUTED KETENES

KW - ASPERGILLUS-FUMIGATUS

KW - ASYMMETRIC-SYNTHESIS

KW - SPIROTRYPROSTATIN-B

KW - RADICAL CYCLIZATION

U2 - 10.1016/j.tet.2010.03.047

DO - 10.1016/j.tet.2010.03.047

M3 - Article

SN - 0040-4020

VL - 66

SP - 3801

EP - 3813

JO - Tetrahedron

JF - Tetrahedron

IS - 21

ER -

Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (+/-)-N-benzyl-coerulescine and (+/-)-horsfiline

Abstract

Keywords

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