Direct Synthesis of β-Hydroxy-α-amino Acids via Diastereoselective Decarboxylative Aldol Reaction

被引：30

作者：

Singjunla, Yuttapong ^{[1
]}

Baudoux, Jerome ^{[1
]}

Rouden, Jacques ^{[1
]}

机构：

[1] ENSICAEN Univ Caen, Lab Chim Mol & Thioorgan, CNRS, Inst Normand Chim Mol Med & Macromol INC3M, F-14050 Caen, France

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 22期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; HALF-THIOESTERS; ENANTIOSELECTIVE SYNTHESIS; POLYKETIDE SYNTHASES; EFFICIENT; ESTERS; 1,4-ADDITION; GLYCINE; ANALOGS; COMPLEX;

D O I：

10.1021/ol402805f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward metal-free synthesis of anti-beta-hydroxy-alpha-amino acids is described. The organic base-mediated decarboxylative aldol reaction of cheap, readily available alpha-amidohemimalonates with various aldehydes afforded under very mild conditions anti-beta-hydroxy-alpha-amido esters in high yields and complete diastereoselectivity. Simple one-pot subsequent transformations enabled the corresponding anti-beta-hydroxy-alpha-amino acids or in a few examples their syn diastereomers to be obtained directly using epimerization conditions.

引用

页码：5770 / 5773

页数：4

共 50 条

[1] Enantioselective Synthesis of anti-β-Hydroxy-α-amino Esters via an Organocatalyzed Decarboxylative Aldol Reaction
March, Taryn
Murata, Akihiro
Kobayashi, Yusuke
Takemoto, Yoshiji
SYNLETT, 2017, 28 (11) : 1295 - 1299
[2] A direct catalytic aldol route to protected β-hydroxy-α-amino acids
Willis, MC
Piccio, VJD
SYNLETT, 2002, (10) : 1625 - 1628
[3] Efficient Synthesis of β-Hydroxy-α-Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imide with Aldehydes
Chen, Xiaohong
Zhu, Yin
Qiao, Zhen
Xie, Mingsheng
Lin, Lili
Liu, Xiaohua
Feng, Xiaoming
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) : 10124 - 10129
[4] Asymmetric Synthesis of β-Hydroxy-α-amino Phosphonic Acid Derivatives via Organocatalytic Direct Aldol Reaction of α-Isothiocyanato Phosphonates with Aldehydes
Han, Wen-Yong
Zhao, Jian-Qiang
Wu, Zhi-Jun
Zhang, Xiao-Mei
Yuan, Wei-Cheng
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20): : 10541 - 10547
[5] Enantioselective construction of β-hydroxy-α,α-disubstituted α-amino acid derivatives via direct aldol reaction of α-imino esters
Araki, Yuya
Hanada, Masato
Iguchi, Yoshiko
Mizoguchi, Haruki
Sakakura, Akira
TETRAHEDRON, 2022, 110
[6] Catalytic asymmetric synthesis of β-hydroxy-α-amino acid esters by direct aldol reaction of glycinate Schiff bases
Yoshikawa, N
Shibasaki, M
TETRAHEDRON, 2002, 58 (41) : 8289 - 8298
[7] Concise enantio- and diastereoselective synthesis of α-hydroxy-α-methyl-β-amino acids
Roers, R
Verdine, GL
TETRAHEDRON LETTERS, 2001, 42 (21) : 3563 - 3565
[8] Biocatalytic synthesis of non-standard amino acids by a decarboxylative aldol reaction
Jonathan M. Ellis
Meghan E. Campbell
Prasanth Kumar
Eric P. Geunes
Craig A. Bingman
Andrew R. Buller
Nature Catalysis, 2022, 5 : 136 - 143
[9] Biocatalytic synthesis of non-standard amino acids by a decarboxylative aldol reaction
Ellis, Jonathan M.
Campbell, Meghan E.
Kumar, Prasanth
Geunes, Eric P.
Bingman, Craig A.
Buller, Andrew R.
NATURE CATALYSIS, 2022, 5 (02) : 136 - +
[10] A new diastereoselective approach to the synthesis of α-hydroxy-β-amino acids based on the frame of captodative olefins
Herrera, R
Jiménez-Vázquez, HA
Tamariz, J
ARKIVOC, 2005, : 233 - 249

← 1 2 3 4 5 →