Synthesis of orthogonally protected biaryl amino acid derivatives

被引：13

作者：

Moreno, Eduardo ^{[1
]}

Antonio Nolasco, Luca ^{[1
]}

Caggiano, Lorenzo ^{[1
]}

Jackson, Richard F. W. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 19期

关键词：

D O I：

10.1039/b609360d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient and direct synthesis of protected biaryl amino acids, including dityrosine (50% overall yield over 3 steps), by Negishi cross-coupling of the serine-derived organozinc reagent 4 with iodo- and di-iodobiaryls, is reported. An improved, although still not perfect, diiodination of 2,2'-biphenol has been achieved using NMe3BnICl2-ZnCl2. Protection of phenolic hydroxyl groups as acetates, rather than benzyl ethers, is required for efficient cross-coupling, and evidence for acetyl migration has been observed during debenzylation of a substituted 2-acetoxy-2'-benzyloxybiaryl. Aromatic C-I to C-Cl conversion has been detected as a minor reaction pathway in the palladium-catalyzed coupling of aryl iodide 3b with organozinc reagent 4.

引用

页码：3639 / 3647

页数：9

共 50 条

[11] Efficient synthesis of orthogonally protected spermidine and norspermidine derivatives
Andruszkiewicz, R
Radowski, M
Czajgucki, Z
[J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (08) : 1085 - 1094
[12] Synthesis of a series of "cationic", orthogonally protected, α,α-disubstituted amino acids
Yokum, TS
Bursavich, MG
Piha-Paul, SA
Hall, DA
McLaughlin, ML
[J]. PEPTIDES: FRONTIERS OF PEPTIDES SCIENCE, 1999, : 329 - 330
[13] SYNTHESIS OF ORTHOGONALLY PROTECTED ACTINOIDIC ACID TRIMETHYL ETHER
Amino, Yusuke
Williams, Robert M.
[J]. HETEROCYCLES, 2019, 99 (01) : 83 - 92
[14] Chiral Phosphoric Acid Catalyzed Asymmetric Hydrolysis of Biaryl Oxazepines for the Synthesis of Axially Chiral Biaryl Amino Phenol Derivatives
Wei, Liwen
Li, Jiaomeng
Zhao, Yi
Zhou, Qinglong
Wei, Zhikang
Chen, Yuhang
Zhang, Xinglong
Yang, Xing
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (39)
[15] Synthesis of orthogonally protected cyclic homooligomers from sugar amino acids
Ménand, M
Blais, JC
Hamon, L
Valéry, JM
Xie, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11): : 4423 - 4430
[16] Efficient synthesis of protected β-amino acid derivatives via asymmetric hydrogenation
Dai, Q
Yang, WR
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3426 - U3426
[17] SYNTHESIS OF SOME PROTECTED AMINO ACID-9-METHOXYPSORALENE DERIVATIVES
ELGAMAL, MHA
ELNAGGAR, AM
ELTAWIL, BAH
AHMED, FSM
[J]. ACTA CHIMICA ACADEMIAE SCIENTARIUM HUNGARICAE, 1976, 91 (04): : 441 - 444
[18] Stereoconservative synthesis of orthogonally protected gamma-functionalized amino acids using N-tritylserine derivatives
Dugave, C
Menez, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17): : 6067 - 6070
[19] Seteroconservative Synthesis of Orthogonally Protected gamma-Functionalized Amino Acids Using N-Tritylserine Derivatives
[J]. J Org Chem, 17 (6067):
[20] Synthesis of orthogonally protected τ-histidinoalanine
Taylor, Carol M.
Batton, Chyree S.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245

← 1 2 3 4 5 →