Asymmetric [4+2]-Cycloaddition of Copper-Allenylidenes with Hexahydro-1,3,5-triazines: Access to Chiral Tetrahydroquinazolines

被引：79

作者：

Ji, Danqing ^{[1
]}

Wang, Cheng ^{[1
]}

Sun, Jiangtao ^{[1
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 12期

基金：

中国国家自然科学基金;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; PROPARGYLIC ESTERS; ENANTIOSELECTIVE PROPARGYLATION; 3+2 CYCLOADDITION; BETA-KETOESTERS; 1,3,5-TRIAZINANES; DEAROMATIZATION; ANNULATION; COMPLEXES; IMINES;

D O I：

10.1021/acs.orglett.8b01584

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed asymmetric formal [4 + 2]-cycloaddition of copper-allenylidenes and hexahydro-1,3,5-triazines has been developed, providing chiral tetrahydroquinazolines in moderate to good yields and with high enantioselectivities for most cases (up to 88% yield and 98% ee).

引用

页码：3710 / 3713

页数：4

共 50 条

[11] Heterocycles from Heterocycles. -III. 1,3,5-Trisubstituted Hexahydro-1,3,5-triazines-2-ones from 1,3,5-Trisubstituted Hexahydro-1,3,5-triazines and Organic Isocyanates
Verardo, G.
Giumanini, A. G.
Gorassini, F.
Strazzolini, P.
Journal of Heterocyclic Chemistry, 32 (03):
[12] Rhodium(II)-Catalyzed [4+2] Annulation of Ester-Tethered 1-Sulfonyl-1,2,3-Triazoles and Hexahydro-1,3,5-Triazines
Duan, Shengguo
Meng, Hui
Jablasone, Saygbechi T., Jr.
Luo, Huan
Xu, Ze-Feng
Li, Chuan-Ying
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (05) : 1076 - 1080
[13] Organocatalytic asymmetric [3+2]-cycloaddition of 3-isothiocyanato oxindoles with 1,3,5-trisubstituted-hexahydro-1,3,5-triazines to access spiro-imidazolidinethione-oxindoles
Zhang, Chuan-Bao
Dou, Pei-Hao
You, Yong
Wang, Zhen-Hua
Zhou, Ming-Qiang
Xu, Xiao-Ying
Yuan, Wei-Cheng
TETRAHEDRON, 2019, 75 (40)
[14] Synthesis of hexahydro-1,3,5-triazines:: A new approach from N-substituted-α-aminoisothiocyanates
Kumar, H
Goyal, R
Parmar, A
Kaur, S
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2006, 45 (02): : 552 - 557
[15] Access to Chiral Tetrahydroquinazolines/1,3-Benzoxazines via Iridium-Catalyzed Asymmetric [4+2] Cycloaddition
Tang, Shengbiao
Cheng, Zhangru
Zhang, Peng
Shao, Ying
Sun, Jiangtao
ORGANIC LETTERS, 2023, 25 (20) : 3639 - 3643
[16] ON 1,3,5-TRIAZINES .2. SYNTHESIS OF 2,4-DITHIO-3,5-DIARYL-6-PHENYLIMINO-HEXAHYDRO-1,3,5-TRIAZINES AND 2,6-DITHIO-3,5-DIARYL-4-PHENYLIMINO-HEXAHYDRO-1,3,5-TRIAZINES
PATHE, PP
AMBEKAR, MW
NIMDEOKAR, NM
PARANJPE, MG
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1982, 59 (05) : 670 - 672
[17] SYNTHESIS AND ATTEMPTED [4+2] CYCLOADDITION REACTION OF 2,4,6-TRIS(PHENYLSELENO)-1,3,5-TRIAZINES AND 2,4,6-TRIS(ARYLTELLURO)-1,3,5-TRIAZINES WITH DIETHYL ACETYLENEDICARBOXYLATE
TANI, H
INAMASU, T
SUZUKI, H
HETEROCYCLES, 1992, 34 (02) : 341 - 347
[18] Metal-free [2+1+3] Cycloaddition of Trifluoroacetaldehyde N-Sulfonylhydrazones with Hexahydro-1,3,5-triazines Leading to Trifluoromethylated 2,3,4,5-Tetrahydro-1,2,4-triazines
Fang, Zhongxue
Jin, Qihao
Wang, Xinyu
Ning, Yongquan
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (05): : 2966 - 2974
[19] Trisubstituted 1,3,5-triazines. 2. Synthesis of 1,3,5-triazines on the basis of 2,4,6-tris[(tert-butoxycarbonyl)methylene]hexahydro-1,3,5-triazine
Shastin, AV
Godovikova, TI
Korsunsky, BL
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (10): : 1404 - 1407
[20] SYNTHESIS OF HEXAHYDRO-1,3,5-TRIAZINES - A NEW APPROACH FROM N-SUBSTITUTED-ALPHA-AMINOISOTHIOCYANATES
KUMAR, B
KUMAR, H
ARORA, S
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1993, 32 (07): : 779 - 782

← 1 2 3 4 5 →