The Enantioselective Synthesis of Chiral Carbocyclic Nucleosides via Palladium-Catalyzed Asymmetric Allylic Amination of Alicyclic MBH Adducts with Purines

被引：16

作者：

Kang, Bo ^{[1
]}

Zhang, Qi-Ying ^{[1
]}

Qu, Gui-Rong ^{[1
]}

Guo, Hai-Ming ^{[1
]}

机构：

[1] Henan Normal Univ, Henan Key Lab Organ Funct Mol & Drug Innovat, Key Lab Green Chem Media & React,Sch Chem & Chem, Minist Educ,Collaborat Innovat Ctr Henan Prov Gre, Xinxiang 453007, Henan, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 10期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; chiral carbocyclic nucleosides; allylic amination; alicyclic MBH adducts; METHYLENECYCLOPROPANE ANALOGS; STEREOSELECTIVE-SYNTHESIS; ANTIVIRAL ACTIVITY; POTENT; DERIVATIVES; INHIBITOR; 1592U89; LIGAND;

D O I：

10.1002/adsc.202000088

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The enantioselective synthesis of carbocyclic nucleosides through the palladium-catalyzed asymmetric allylic amination of alicyclic Morita-Baylis-Hillman (MBH) adducts with purines was successfully developed. With a combination of Pd-2 (dba)(3)/L7 as catalyst, various optically active carbocyclic nucleosides featuring a C=C double bond in the carbocycle moiety were obtained in high yields (up to 97%) with excellent N-9/N-7-selectivities (> 95/5) and enantioselectivities (up to > 99.6%). In addition, these nucleoside analogs allowed for rapid transformation to a variety of other interesting structurally diverse chiral carbocyclic nucleosides.

引用

页码：1955 / 1960

页数：6

共 50 条

[11] Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed annulation with diarylethynes
Shi, Yan-Chao
Yang, Rong-Fei
Gao, De-Wei
You, Shu-Li
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1891 - 1896
[12] Regioselective Synthesis of Optically Active Trifluoromethyl Group Substituted Allylic Amines by Palladium-Catalyzed Allylic Amination
Hirakawa, Takuya
Ikeda, Kazunori
Ogasa, Hiroshi
Kawatsura, Motoi
Itoh, Toshiyuki
SYNLETT, 2010, (19) : 2887 - 2890
[13] Palladium-catalyzed asymmetric allylic substitution using planar chiral hydrazone ligands
Mino, T
Ogawa, T
Yamashita, M
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 665 (1-2) : 122 - 126
[14] Enantioselective Construction of Quaternary Carbon Stereocenter via Palladium-Catalyzed Asymmetric Allylic Alkylation of Lactones
Li, Xiao-Hui
Wan, Shi-Li
Chen, Di
Liu, Qing Rong
Ding, Chang-Hua
Fang, Ping
Hou, Xue-Long
SYNTHESIS-STUTTGART, 2016, 48 (10): : 1568 - 1572
[15] Enantioselective Formal Synthesis of Nectrisine Using a Palladium Catalyzed Asymmetric Allylic Amination and Cross-Metathesis as Key Steps
Soriano, Sebastien
Azzouz, Mariam
Llaveria, Josep
Marce, Patricia
Isabel Matheu, M.
Diaz, Yolanda
Castillon, Sergio
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (12): : 5217 - 5221
[16] Chiral hydrazones as ligands in asymmetric catalysts: Palladium-catalyzed allylic substitution
Mino, T
Imiya, W
Yamashita, M
SYNLETT, 1997, (05) : 583 - &
[17] Enantioselective Synthesis of Tertiary a-Hydroxyketones from Unfunctionalized Ketones: Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates
Trost, Barry M.
Koller, Raffael
Schaeffner, Benjamin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (33) : 8290 - 8293
[18] Asymmetric Formal Synthesis of (-)-Cephalotaxine via Palladium-Catalyzed Enantioselective Tsuji Allylation
Zhang, Zhi-Wei
Wang, Cui-Cui
Xue, Hong
Dong, Yu
Yang, Jian-Hua
Liu, Shouxin
Liu, Wen-Qing
Li, Wei-Dong Z.
ORGANIC LETTERS, 2018, 20 (04) : 1050 - 1053
[19] Enantioselective Synthesis of Dialkylated N-Heterocycles by Palladium-Catalyzed Allylic Alkylation
Numajiri, Yoshitaka
Jimenez-Oses, Gonzalo
Wang, Bo
Houk, K. N.
Stoltz, Brian M.
ORGANIC LETTERS, 2015, 17 (05) : 1082 - 1085
[20] Synthesis of chiral S,N-thioimidazoline ligands for palladium-catalyzed asymmetric allylic allcylations
Hao, Xin-Qi
Shen, Ming-Zhan
Jian, Ning-Ge
Pang, Wei
Shen, Xiao-Jing
Zhu, Xinju
Song, Mao-Ping
TETRAHEDRON-ASYMMETRY, 2016, 27 (4-5) : 163 - 170

← 1 2 3 4 5 →