Hydroboration-Suzuki cross coupling of unsaturated amino acids; the synthesis of pyrimine derivatives

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

Hydroboration-Suzuki cross coupling of unsaturated amino acids; the synthesis of pyrimine derivatives

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

Chemistry

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

Abstract

Hydroboration of protected allylglycines with 9-BBN followed by Suzuki cross coupling of the resulting organoboranes proceeded smoothly giving a range of new bis-homophenylalanine and related derivatives in good yields (9 examples, 53-64%). One of the Suzuki coupling products has been elaborated to give the N-Cbz-protected natural product pyrimine. The hydroboration-Suzuki coupling of vinylglycine derivatives was also studied but was less efficient than with the allylglycine derivatives: the best results were obtained using disiamylborane(.)DMS as the hydroborating agent. (C) 2002 Published by Elsevier Science Ltd.

Original language	English
Pages (from-to)	6117-6125
Number of pages	9
Journal	Tetrahedron
Volume	58
Issue number	30
Publication status	Published - 22 Jul 2002

Keywords

hydroboration-Suzuki cross coupling
unsaturated amino acids
pyrimine derivatives
STEREOSELECTIVE SYNTHESIS
ASPARTIC-ACID
PURE BETA
ORGANOZINC REAGENTS
SERINE
CONVERSION
DAP
AZIRIDINE-2-CARBOXYLATES
HOMOPHENYLALANINE
PHENYLALANINE

Cite this

@article{2766141df4034520806ca759397e47b4,

title = "Hydroboration-Suzuki cross coupling of unsaturated amino acids; the synthesis of pyrimine derivatives",

abstract = "Hydroboration of protected allylglycines with 9-BBN followed by Suzuki cross coupling of the resulting organoboranes proceeded smoothly giving a range of new bis-homophenylalanine and related derivatives in good yields (9 examples, 53-64%). One of the Suzuki coupling products has been elaborated to give the N-Cbz-protected natural product pyrimine. The hydroboration-Suzuki coupling of vinylglycine derivatives was also studied but was less efficient than with the allylglycine derivatives: the best results were obtained using disiamylborane(.)DMS as the hydroborating agent. (C) 2002 Published by Elsevier Science Ltd.",

keywords = "hydroboration-Suzuki cross coupling, unsaturated amino acids, pyrimine derivatives, STEREOSELECTIVE SYNTHESIS, ASPARTIC-ACID, PURE BETA, ORGANOZINC REAGENTS, SERINE, CONVERSION, DAP, AZIRIDINE-2-CARBOXYLATES, HOMOPHENYLALANINE, PHENYLALANINE",

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

year = "2002",

month = jul,

day = "22",

language = "English",

volume = "58",

pages = "6117--6125",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "30",

}

TY - JOUR

T1 - Hydroboration-Suzuki cross coupling of unsaturated amino acids; the synthesis of pyrimine derivatives

AU - Collier, P N

AU - Campbell, A D

AU - Patel, I

AU - Taylor, R J K

PY - 2002/7/22

Y1 - 2002/7/22

N2 - Hydroboration of protected allylglycines with 9-BBN followed by Suzuki cross coupling of the resulting organoboranes proceeded smoothly giving a range of new bis-homophenylalanine and related derivatives in good yields (9 examples, 53-64%). One of the Suzuki coupling products has been elaborated to give the N-Cbz-protected natural product pyrimine. The hydroboration-Suzuki coupling of vinylglycine derivatives was also studied but was less efficient than with the allylglycine derivatives: the best results were obtained using disiamylborane(.)DMS as the hydroborating agent. (C) 2002 Published by Elsevier Science Ltd.

AB - Hydroboration of protected allylglycines with 9-BBN followed by Suzuki cross coupling of the resulting organoboranes proceeded smoothly giving a range of new bis-homophenylalanine and related derivatives in good yields (9 examples, 53-64%). One of the Suzuki coupling products has been elaborated to give the N-Cbz-protected natural product pyrimine. The hydroboration-Suzuki coupling of vinylglycine derivatives was also studied but was less efficient than with the allylglycine derivatives: the best results were obtained using disiamylborane(.)DMS as the hydroborating agent. (C) 2002 Published by Elsevier Science Ltd.

KW - hydroboration-Suzuki cross coupling

KW - unsaturated amino acids

KW - pyrimine derivatives

KW - STEREOSELECTIVE SYNTHESIS

KW - ASPARTIC-ACID

KW - PURE BETA

KW - ORGANOZINC REAGENTS

KW - SERINE

KW - CONVERSION

KW - DAP

KW - AZIRIDINE-2-CARBOXYLATES

KW - HOMOPHENYLALANINE

KW - PHENYLALANINE

M3 - Article

SN - 0040-4020

VL - 58

SP - 6117

EP - 6125

JO - Tetrahedron

JF - Tetrahedron

IS - 30

ER -