First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed α-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement

Brij Bhushan Ahuja; Arumugam Sudalai

doi:10.1016/j.tetasy.2015.03.011

First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed α-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement

Brij Bhushan Ahuja, Arumugam Sudalai^*

^*Corresponding author for this work

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

Abstract

Abstract: A concise enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine with an overall yield of 10.9% and 98% ee, starting from commercially available 1,4-butanediol in ten linear steps has been achieved. The key chiral inducing steps are d-proline catalyzed sequential α-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the subsequent diastereoselective MOM-ether-directed Pd-catalyzed aza-Claisen rearrangement of allylic trichloroacetimidate.

Original language	English
Article number	59293
Pages (from-to)	548-552
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	26
Issue number	10-11
DOIs	https://doi.org/10.1016/j.tetasy.2015.03.011
State	Published - 31 May 2015
Externally published	Yes

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title = "First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed α-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement",

abstract = "Abstract: A concise enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine with an overall yield of 10.9% and 98% ee, starting from commercially available 1,4-butanediol in ten linear steps has been achieved. The key chiral inducing steps are d-proline catalyzed sequential α-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the subsequent diastereoselective MOM-ether-directed Pd-catalyzed aza-Claisen rearrangement of allylic trichloroacetimidate.",

author = "Ahuja, {Brij Bhushan} and Arumugam Sudalai",

note = "Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = may,

day = "31",

doi = "10.1016/j.tetasy.2015.03.011",

language = "אנגלית",

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T1 - First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed α-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement

AU - Ahuja, Brij Bhushan

AU - Sudalai, Arumugam

PY - 2015/5/31

Y1 - 2015/5/31

N2 - Abstract: A concise enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine with an overall yield of 10.9% and 98% ee, starting from commercially available 1,4-butanediol in ten linear steps has been achieved. The key chiral inducing steps are d-proline catalyzed sequential α-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the subsequent diastereoselective MOM-ether-directed Pd-catalyzed aza-Claisen rearrangement of allylic trichloroacetimidate.

AB - Abstract: A concise enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine with an overall yield of 10.9% and 98% ee, starting from commercially available 1,4-butanediol in ten linear steps has been achieved. The key chiral inducing steps are d-proline catalyzed sequential α-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the subsequent diastereoselective MOM-ether-directed Pd-catalyzed aza-Claisen rearrangement of allylic trichloroacetimidate.

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SN - 0957-4166

VL - 26

SP - 548

EP - 552

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 10-11

M1 - 59293

ER -

First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed α-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement

Abstract

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