Enantiomerically pure alpha-amino acid synthesis via hydroboration - Suzuki cross-coupling

P N  Collier; A D  Campbell; I  Patel; T M  Raynham; R J K  Taylor

doi:10.1021/jo010865a

Enantiomerically pure alpha-amino acid synthesis via hydroboration - Suzuki cross-coupling

P N Collier, A D Campbell, I Patel, T M Raynham, R J K Taylor

Chemistry

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

Abstract

The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis-oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient. Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

Original language	English
Pages (from-to)	1802-1815
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	67
Issue number	6
DOIs	https://doi.org/10.1021/jo010865a
Publication status	Published - 22 Mar 2002

Keywords

SIMPLE ASYMMETRIC-SYNTHESIS
STEREOSELECTIVE SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
2,7-DIAMINOSUBERIC ACID
DERIVATIVES
BETA
SERINE
ANALOGS
ESTERS
OXAZOLIDINE

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10.1021/jo010865a

Cite this

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title = "Enantiomerically pure alpha-amino acid synthesis via hydroboration - Suzuki cross-coupling",

abstract = "The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis-oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient. Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.",

keywords = "SIMPLE ASYMMETRIC-SYNTHESIS, STEREOSELECTIVE SYNTHESIS, ENANTIOSELECTIVE SYNTHESIS, 2,7-DIAMINOSUBERIC ACID, DERIVATIVES, BETA, SERINE, ANALOGS, ESTERS, OXAZOLIDINE",

author = "Collier, {P N} and Campbell, {A D} and I Patel and Raynham, {T M} and Taylor, {R J K}",

year = "2002",

month = mar,

day = "22",

doi = "10.1021/jo010865a",

language = "English",

volume = "67",

pages = "1802--1815",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Enantiomerically pure alpha-amino acid synthesis via hydroboration - Suzuki cross-coupling

AU - Collier, P N

AU - Campbell, A D

AU - Patel, I

AU - Raynham, T M

AU - Taylor, R J K

PY - 2002/3/22

Y1 - 2002/3/22

N2 - The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis-oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient. Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

AB - The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis-oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient. Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

KW - SIMPLE ASYMMETRIC-SYNTHESIS

KW - STEREOSELECTIVE SYNTHESIS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - 2,7-DIAMINOSUBERIC ACID

KW - DERIVATIVES

KW - BETA

KW - SERINE

KW - ANALOGS

KW - ESTERS

KW - OXAZOLIDINE

U2 - 10.1021/jo010865a

DO - 10.1021/jo010865a

M3 - Article

SN - 0022-3263

VL - 67

SP - 1802

EP - 1815

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -