Organocatalytic Asymmetric Mannich Addition of 3-Fluorooxindoles to Dibenzo[b,f][1,4]oxazepines: Highly Enantioselective Construction of Tetrasubstituted C-F Stereocenters

被引：20

作者：

Li, Bing-Yu ^{[1
]}

Lin, Ye ^{[1
]}

Du, Da-Ming ^{[1
]}

机构：

[1] Beijing Inst Technol, Sch Chem & Chem Engn, Beijing 100081, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 18期

基金：

中国国家自然科学基金;

关键词：

HIV-1; REVERSE-TRANSCRIPTASE; NONNUCLEOSIDE INHIBITORS; MICHAEL ADDITION; FLUORINE; DERIVATIVES; ACCESS; STEREOSELECTIVITY; DIBENZOXAZEPINES; PHARMACOLOGY; NITROALKENES;

D O I：

10.1021/acs.joc.9b01507

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Fluorooxindoles and the dibenzo[b,f][1,4]oxazepane scaffolds are important pharmacophores that have important application in medicinal chemistry. An organocatalyzed asymmetric Mannich reaction of 3-fluorooxindoles with dibenzo[b,f][1,4]oxazepines affording various seven-member cyclic amines containing chiral tetrasubstituted C-F stereocenters was developed. These reactions which were catalyzed by a bifunctional Cinchona alkaloid-derived thiourea catalyst afforded a wide range of substrates in moderate to high yields with excellent diastereo- and enantioselectivities (up to 88% yield, >20:1 dr and >99% ee). A feasible reaction mechanism was also proposed.

引用

页码：11752 / 11762

页数：11

共 62 条

[21] AMOXAPINE - A REVIEW OF ITS PHARMACOLOGY AND EFFICACY IN DEPRESSED STATES
JUE, SG
DAWSON, GW
BROGDEN, RN
[J]. DRUGS, 1982, 24 (01) : 1 - 23
[22] NOVEL NONNUCLEOSIDE INHIBITORS OF HIV-1 REVERSE-TRANSCRIPTASE .2. TRICYCLIC PYRIDOBENZOXAZEPINONES AND DIBENZOXAZEPINONES
KLUNDER, JM
HARGRAVE, KD
WEST, MA
CULLEN, E
PAL, K
BEHNKE, ML
KAPADIA, SR
MCNEIL, DW
WU, JC
CHOW, GC
ADAMS, J
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (10) : 1887 - 1897
[23] Practical synthesis of fluorine-containing α- and β-amino acids: recipes from Kiev, Ukraine
Kukhar, Valery P.
Sorochinsky, Alexander E.
Soloshonok, Vadim A.
[J]. FUTURE MEDICINAL CHEMISTRY, 2009, 1 (05) : 793 - 819
[24] Chiral Squaramide-Catalyzed Asymmetric Mannich Reactions for Synthesis of Fluorinated 3,3-Bisoxindoles
Li, Bing-Yu
Du, Da-Ming
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (16) : 3164 - 3170
[25] Notable and obvious ketene substituent-dependent effect of temperature on the stereoselectivity in the Staudinger reaction
Li, Bonan
Wang, Yikai
Du, Da-Ming
Xu, Jiaxi
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) : 990 - 997
[26] Access to Chiral Seven-Member Cyclic Amines via Rh-Catalyzed Asymmetric Hydrogenation
Li, Pan
Huang, Yi
Hu, Xinquan
Dong, Xiu-Qin
Zhang, Xumu
[J]. ORGANIC LETTERS, 2017, 19 (14) : 3855 - 3858
[27] Li R, 1995, Drug Des Discov, V12, P337
[28] Introduction of Fluorine and Fluorine-Containing Functional Groups
Liang, Theresa
Neumann, Constanze N.
Ritter, Tobias
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (32) : 8214 - 8264
[29] PYRIDOBENZOXAZEPINE AND PYRIDOBENZOTHIAZEPINE DERIVATIVES AS POTENTIAL CENTRAL-NERVOUS-SYSTEM AGENTS - SYNTHESIS AND NEUROCHEMICAL STUDY
LIEGEOIS, JFF
ROGISTER, FA
BRUHWYLER, J
DAMAS, J
NGUYEN, TP
INAREJOS, MO
CHLEIDE, EMG
MERCIER, MGA
DELARGE, JE
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (04) : 519 - 525
[30] Organocatalytic Enantioselective Strecker Reaction with Seven-Membered Cyclic Imines
Lluna-Galan, Carles
Blay, Gonzalo
Fernandez, Isabel
Carmen Munoz, M.
Pedro, Jose R.
Vila, Carlos
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (19) : 3662 - 3666

← 1 2 3 4 5 6 7 →