Diastereoselective conjugate reduction with samarium diiodide: Asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate

Stephen G. Davies; Humberto Rodríguez-Solla; Juan A. Tamayo; A. Christopher Garner; Andrew D. Smith

doi:10.1039/b408257e

Diastereoselective conjugate reduction with samarium diiodide: Asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate

Stephen G. Davies^*
, Humberto Rodríguez-Solla
, Juan A. Tamayo
, A. Christopher Garner
, Andrew D. Smith

^*Corresponding author for this work

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

Abstract

A highly diastereoselective conjugate reduction using SmI₂ and D₂O has been demonstrated on a homochiral benzylidene diketopiperazine template, giving methyl (2S,3R)-N-acetyl-2-amino-2,3- dideuterio-3-phenylpropionate 12 in 93% de and 90% ee after deprotection, hydrolysis and N-acetylation.

Original language	English
Pages (from-to)	2502-2503
Number of pages	2
Journal	Chemical Communications
Volume	10
Issue number	21
DOIs	https://doi.org/10.1039/b408257e
Publication status	Published - 7 Nov 2004

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title = "Diastereoselective conjugate reduction with samarium diiodide: Asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate",

abstract = "A highly diastereoselective conjugate reduction using SmI2 and D2O has been demonstrated on a homochiral benzylidene diketopiperazine template, giving methyl (2S,3R)-N-acetyl-2-amino-2,3- dideuterio-3-phenylpropionate 12 in 93\% de and 90\% ee after deprotection, hydrolysis and N-acetylation.",

author = "Davies, \{Stephen G.\} and Humberto Rodr{\'i}guez-Solla and Tamayo, \{Juan A.\} and Garner, \{A. Christopher\} and Smith, \{Andrew D.\}",

year = "2004",

month = nov,

day = "7",

doi = "10.1039/b408257e",

language = "English",

volume = "10",

pages = "2502--2503",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "21",

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TY - JOUR

T1 - Diastereoselective conjugate reduction with samarium diiodide

T2 - Asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate

AU - Davies, Stephen G.

AU - Rodríguez-Solla, Humberto

AU - Tamayo, Juan A.

AU - Garner, A. Christopher

AU - Smith, Andrew D.

PY - 2004/11/7

Y1 - 2004/11/7

N2 - A highly diastereoselective conjugate reduction using SmI2 and D2O has been demonstrated on a homochiral benzylidene diketopiperazine template, giving methyl (2S,3R)-N-acetyl-2-amino-2,3- dideuterio-3-phenylpropionate 12 in 93% de and 90% ee after deprotection, hydrolysis and N-acetylation.

AB - A highly diastereoselective conjugate reduction using SmI2 and D2O has been demonstrated on a homochiral benzylidene diketopiperazine template, giving methyl (2S,3R)-N-acetyl-2-amino-2,3- dideuterio-3-phenylpropionate 12 in 93% de and 90% ee after deprotection, hydrolysis and N-acetylation.

UR - https://www.scopus.com/pages/publications/9444287694

U2 - 10.1039/b408257e

DO - 10.1039/b408257e

M3 - Article

C2 - 15514836

AN - SCOPUS:9444287694

SN - 1359-7345

VL - 10

SP - 2502

EP - 2503

JO - Chemical Communications

JF - Chemical Communications

IS - 21

ER -

Diastereoselective conjugate reduction with samarium diiodide: Asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate

Abstract

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