An expedient asymmetric synthesis of N-protected (S,S)-2-Aminomethyl-1-cyclopropanecarboxylic acid

D J Aitken; Steven D Bull; Iwan R Davies; L Drouin; J Ollivier; Jennifer Peed

doi:10.1055/s-0030-1258814

An expedient asymmetric synthesis of N-protected (S,S)-2-Aminomethyl-1-cyclopropanecarboxylic acid

D J Aitken, Steven D Bull, Iwan R Davies, L Drouin, J Ollivier, Jennifer Peed

Department of Chemistry

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

19 Citations (SciVal)

Abstract

An enantioselective synthesis of a N-Boc-protected trans-cyclopropane gamma-amino acid is reported. The key chiral aldehyde intermediate is prepared in enantiomerically pure form using a three-step aldol-cyclopropanation-retro-aldol protocol.

Original language	English
Pages (from-to)	2729-2732
Number of pages	4
Journal	Synlett
Volume	18
DOIs	https://doi.org/10.1055/s-0030-1258814
Publication status	Published - Nov 2010

Keywords

enantioselectivity
carbocycle
asymmetric synthesis
aldol reaction
amino acids
chiral auxiliary

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abstract = "An enantioselective synthesis of a N-Boc-protected trans-cyclopropane gamma-amino acid is reported. The key chiral aldehyde intermediate is prepared in enantiomerically pure form using a three-step aldol-cyclopropanation-retro-aldol protocol.",

keywords = "enantioselectivity, carbocycle, asymmetric synthesis, aldol reaction, amino acids, chiral auxiliary",

author = "Aitken, {D J} and Bull, {Steven D} and Davies, {Iwan R} and L Drouin and J Ollivier and Jennifer Peed",

year = "2010",

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T1 - An expedient asymmetric synthesis of N-protected (S,S)-2-Aminomethyl-1-cyclopropanecarboxylic acid

AU - Aitken, D J

AU - Bull, Steven D

AU - Davies, Iwan R

AU - Drouin, L

AU - Ollivier, J

AU - Peed, Jennifer

PY - 2010/11

Y1 - 2010/11

N2 - An enantioselective synthesis of a N-Boc-protected trans-cyclopropane gamma-amino acid is reported. The key chiral aldehyde intermediate is prepared in enantiomerically pure form using a three-step aldol-cyclopropanation-retro-aldol protocol.

AB - An enantioselective synthesis of a N-Boc-protected trans-cyclopropane gamma-amino acid is reported. The key chiral aldehyde intermediate is prepared in enantiomerically pure form using a three-step aldol-cyclopropanation-retro-aldol protocol.

KW - enantioselectivity

KW - carbocycle

KW - asymmetric synthesis

KW - aldol reaction

KW - amino acids

KW - chiral auxiliary

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UR - http://dx.doi.org/10.1055/s-0030-1258814

U2 - 10.1055/s-0030-1258814

DO - 10.1055/s-0030-1258814

M3 - Article

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JO - Synlett

JF - Synlett

ER -

An expedient asymmetric synthesis of N-protected (S,S)-2-Aminomethyl-1-cyclopropanecarboxylic acid

Abstract

Keywords

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