An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation

W. Wang; C. Xiong; J. Yang; Victor J Hruby

doi:10.1055/s-2002-19295

An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation

W. Wang, C. Xiong, J. Yang, Victor J Hruby

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

22 Scopus citations

Abstract

An efficient synthesis of the title compounds 1 and 2 has been successfully developed. The key step is the asymmetric hydrogenation of dehydroamino acid 7 using [Rh(I)(COD)-(S,S) or - (R,R)-Et-DuPHOS)]⁺OTf^- to produce the optically active, protected amino acid derivatives in high ee (>95%). The approach also can be used for the synthesis of other isomers and analogues.

Original language	English (US)
Pages (from-to)	94-98
Number of pages	5
Journal	Synthesis
Issue number	1
DOIs	https://doi.org/10.1055/s-2002-19295
State	Published - 2002

Keywords

Amino acids
Asymmetric hydrogenation
DAP analogues
Diaminopimelic acids
DuPHOS

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1055/s-2002-19295

Cite this

@article{a21fe276e11b4ff891845e790fc4473c,

title = "An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation",

abstract = "An efficient synthesis of the title compounds 1 and 2 has been successfully developed. The key step is the asymmetric hydrogenation of dehydroamino acid 7 using [Rh(I)(COD)-(S,S) or - (R,R)-Et-DuPHOS)]+OTf- to produce the optically active, protected amino acid derivatives in high ee (>95%). The approach also can be used for the synthesis of other isomers and analogues.",

keywords = "Amino acids, Asymmetric hydrogenation, DAP analogues, Diaminopimelic acids, DuPHOS",

author = "W. Wang and C. Xiong and J. Yang and Hruby, {Victor J}",

year = "2002",

doi = "10.1055/s-2002-19295",

language = "English (US)",

pages = "94--98",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "1",

}

TY - JOUR

T1 - An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation

AU - Wang, W.

AU - Xiong, C.

AU - Yang, J.

AU - Hruby, Victor J

PY - 2002

Y1 - 2002

N2 - An efficient synthesis of the title compounds 1 and 2 has been successfully developed. The key step is the asymmetric hydrogenation of dehydroamino acid 7 using [Rh(I)(COD)-(S,S) or - (R,R)-Et-DuPHOS)]+OTf- to produce the optically active, protected amino acid derivatives in high ee (>95%). The approach also can be used for the synthesis of other isomers and analogues.

AB - An efficient synthesis of the title compounds 1 and 2 has been successfully developed. The key step is the asymmetric hydrogenation of dehydroamino acid 7 using [Rh(I)(COD)-(S,S) or - (R,R)-Et-DuPHOS)]+OTf- to produce the optically active, protected amino acid derivatives in high ee (>95%). The approach also can be used for the synthesis of other isomers and analogues.

KW - Amino acids

KW - Asymmetric hydrogenation

KW - DAP analogues

KW - Diaminopimelic acids

KW - DuPHOS

UR - http://www.scopus.com/inward/record.url?scp=0036138441&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036138441&partnerID=8YFLogxK

U2 - 10.1055/s-2002-19295

DO - 10.1055/s-2002-19295

M3 - Article

AN - SCOPUS:0036138441

SN - 0039-7881

SP - 94

EP - 98

JO - Synthesis

JF - Synthesis

IS - 1

ER -

An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this