An Enantioselective Decarboxylative Glycolate Aldol Reaction

被引：0

作者：

Rahman, Md. Ataur ^{[1
]}

Rehan, Mohammad ^{[1
]}

Cellnik, Torsten ^{[1
]}

Ahuja, Brij Bhushan ^{[1
]}

Healy, Alan R. ^{[1
]}

机构：

[1] New York Univ Abu Dhabi NYUAD, Chem Program, Saadiyat Isl, U Arab Emirates

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 42期

关键词：

CATALYTIC ASYMMETRIC-SYNTHESIS; ACID-CONTROLLED SYNTHESIS; LEWIS-BASE ACTIVATION; HYDROXYKETONES; DERIVATIVES; THIOESTERS; KETONES;

D O I：

10.1021/acs.orglett.4c03251

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report the application of a benzyloxy-functionalized malonic acid half thioester as an activated ester equivalent in a highly enantioselective decarboxylative glycolate aldol reaction. This robust method operates at ambient temperature, tolerates air and moisture, and generates CO2 as the only byproduct. The synthetic applicability of the method is demonstrated by the large-scale enantiodivergent synthesis of alpha-benzyloxy-beta-hydroxybutyric acid thioester and its subsequent conversion to diverse polyoxygenated building blocks, deoxy-sugars, and (-)-angiopterlactone B.

引用

页码：9040 / 9045

页数：6

共 50 条

[1] Enantioselective total synthesis of (+)-gigantecin: Exploiting the asymmetric glycolate aldol reaction
Crimmins, MT
She, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (40) : 12790 - 12791
[2] Biomimetic catalytic enantioselective decarboxylative aldol reaction of β-ketoacids with trifluoromethyl ketones
Zheng, Yan
Xiong, Heng-Ying
Nie, Jing
Hua, Ming-Qing
Ma, Jun-An
CHEMICAL COMMUNICATIONS, 2012, 48 (36) : 4308 - 4310
[3] Organocatalytic Enantioselective Decarboxylative Aldol Reaction of Malonic Acid Half Thioesters with Aldehydes
Bae, Han Yong
Sim, Jae Hun
Lee, Ji-Woong
List, Benjamin
Song, Choong Eui
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (46) : 12143 - 12147
[4] Lipase-catalysed decarboxylative aldol reaction and decarboxylative Knoevenagel reaction
Feng, Xing-Wen
Li, Chao
Wang, Na
Li, Kun
Zhang, Wei-Wei
Wang, Zao
Yu, Xiao-Qi
GREEN CHEMISTRY, 2009, 11 (12) : 1933 - 1936
[5] Organocatalytic decarboxylative aldol reaction of β-ketoacids with α-ketophosphonates en route to the enantioselective synthesis of tertiary α-hydroxyphosphonates
Vamisetti, Ganga B.
Chowdhury, Raghunath
Ghosh, Sunil K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (18) : 3869 - 3873
[6] A convenient enantioselective decarboxylative aldol reaction to access chiral α-hydroxy esters using β-keto acids
Duan, Zhiqiang
Han, Jianlin
Qian, Ping
Zhang, Zirui
Wang, Yi
Pan, Yi
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 969 - 974
[7] 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
[8] A catalytic enantioselective stereodivergent aldol reaction
Rahman, Md. Ataur
Cellnik, Torsten
Ahuja, Brij Bhushan
Li, Liang
Healy, Alan R.
SCIENCE ADVANCES, 2023, 9 (11)
[9] Enantioselective aldol reaction catalysed by polyleucines
Carrea, Giacomo
Ottolina, Gianluca
Lazcano, Antonio
Pironti, Vincenza
Colonna, Stefano
TETRAHEDRON-ASYMMETRY, 2007, 18 (11) : 1265 - 1268
[10] Catalytic enantioselective aldol reaction to ketones
Oisaki, Kounosuke
Zhao, Dongbo
Kanai, Motomu
Shibasaki, Masakatsu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) : 7164 - 7165

← 1 2 3 4 5 →