Lithium Amide Conjugate Addition for the Asymmetric Synthesis of 3-Aminopyrrolidines

Stephen G. Davies; A. Christopher Garner; Euan C. Goddard; Dennis Kruchinin; Paul M. Roberts; Humberto Rodriguez-Solla; Andrew D. Smith

doi:10.1039/b604835h

Lithium Amide Conjugate Addition for the Asymmetric Synthesis of 3-Aminopyrrolidines

Stephen G. Davies, A. Christopher Garner, Euan C. Goddard, Dennis Kruchinin, Paul M. Roberts, Humberto Rodriguez-Solla, Andrew D. Smith

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

Abstract

Conjugate addition of homochiral lithium amides to methyl 4-(N-benzyl-N-allylamino) but-2-enoate, chemoselective N-deprotection and concomitant cyclisation, followed by enolate functionalisation and deprotection allows access to syn- and anti-3,4-disubstituted aminopyrrolidines in > 98% d.e. and >98% e.e.

Original language	English
Pages (from-to)	2664-2666
Number of pages	3
Journal	Chemical Communications
Issue number	25
DOIs	https://doi.org/10.1039/b604835h
Publication status	Published - 2006

Keywords

1,3-DIPOLAR CYCLOADDITION
GLYCOSIDASE INHIBITORS
AMMONIA EQUIVALENTS
KINETIC PROTONATION
ACIDS
STEREOCHEMISTRY
DERIVATIVES
AGENTS

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10.1039/b604835h

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@article{c814eef8f07148b9867e88929d577a4d,

title = "Lithium Amide Conjugate Addition for the Asymmetric Synthesis of 3-Aminopyrrolidines",

abstract = "Conjugate addition of homochiral lithium amides to methyl 4-(N-benzyl-N-allylamino) but-2-enoate, chemoselective N-deprotection and concomitant cyclisation, followed by enolate functionalisation and deprotection allows access to syn- and anti-3,4-disubstituted aminopyrrolidines in > 98\% d.e. and >98\% e.e.",

keywords = "1,3-DIPOLAR CYCLOADDITION, GLYCOSIDASE INHIBITORS, AMMONIA EQUIVALENTS, KINETIC PROTONATION, ACIDS, STEREOCHEMISTRY, DERIVATIVES, AGENTS",

author = "Davies, \{Stephen G.\} and Garner, \{A. Christopher\} and Goddard, \{Euan C.\} and Dennis Kruchinin and Roberts, \{Paul M.\} and Humberto Rodriguez-Solla and Smith, \{Andrew D.\}",

year = "2006",

doi = "10.1039/b604835h",

language = "English",

pages = "2664--2666",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "25",

}

TY - JOUR

T1 - Lithium Amide Conjugate Addition for the Asymmetric Synthesis of 3-Aminopyrrolidines

AU - Davies, Stephen G.

AU - Garner, A. Christopher

AU - Goddard, Euan C.

AU - Kruchinin, Dennis

AU - Roberts, Paul M.

AU - Rodriguez-Solla, Humberto

AU - Smith, Andrew D.

PY - 2006

Y1 - 2006

N2 - Conjugate addition of homochiral lithium amides to methyl 4-(N-benzyl-N-allylamino) but-2-enoate, chemoselective N-deprotection and concomitant cyclisation, followed by enolate functionalisation and deprotection allows access to syn- and anti-3,4-disubstituted aminopyrrolidines in > 98% d.e. and >98% e.e.

AB - Conjugate addition of homochiral lithium amides to methyl 4-(N-benzyl-N-allylamino) but-2-enoate, chemoselective N-deprotection and concomitant cyclisation, followed by enolate functionalisation and deprotection allows access to syn- and anti-3,4-disubstituted aminopyrrolidines in > 98% d.e. and >98% e.e.

KW - 1,3-DIPOLAR CYCLOADDITION

KW - GLYCOSIDASE INHIBITORS

KW - AMMONIA EQUIVALENTS

KW - KINETIC PROTONATION

KW - ACIDS

KW - STEREOCHEMISTRY

KW - DERIVATIVES

KW - AGENTS

UR - https://www.scopus.com/pages/publications/33745193911

U2 - 10.1039/b604835h

DO - 10.1039/b604835h

M3 - Article

SN - 1359-7345

SP - 2664

EP - 2666

JO - Chemical Communications

JF - Chemical Communications

IS - 25

ER -

Lithium Amide Conjugate Addition for the Asymmetric Synthesis of 3-Aminopyrrolidines

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