Nickel-Catalyzed Enantioselective Reductive Spirocyclization of 1,6-Enynes with o -Bromobenzaldehydes

被引:1
作者
Guo, Haoyun [1 ]
Chen, Yate [2 ]
Kong, Wangqing [1 ]
机构
[1] Wuhan Univ, Inst Adv Studies IAS, Wuhan 430072, Peoples R China
[2] Huazhong Agr Univ, Coll Chem, Wuhan 430070, Peoples R China
来源
SYNTHESIS-STUTTGART | 2025年 / 57卷 / 08期
基金
中国国家自然科学基金;
关键词
nickel catalysis; enantioselectivity; reductive spirocyclization; 1,6-enynes; spiroindanones; COUPLING REACTIONS; SPIRO COMPOUNDS; CYCLIZATION; HALIDES; NOMENCLATURE;
D O I
10.1055/a-2456-9530
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We developed a Ni-catalyzed asymmetric reductive spirocyclization of 1,6-enynes with o-haloaryl aldehydes. This approach provides an efficient method for the construction of chiral spiroindanone pyrrolidine derivatives in good yields with excellent enantio- and diastereoselectivity (up to 99% ee, >20:1 dr). This reaction does not require pre-prepared organometallic reagents and exhibits excellent substrate compatibility.
引用
收藏
页码:1448 / 1456
页数:9
相关论文
共 53 条
[31]   Ni-Catalyzed Regio- and Enantioselective Domino Reductive Cyclization: One-Pot Synthesis of 2,3-Fused Cyclopentannulated Indolines [J].
Ping, Yuanyuan ;
Wang, Kuai ;
Pan, Qi ;
Ding, Zhengtian ;
Zhou, Zhijun ;
Guo, Ya ;
Kong, Wangqing .
ACS CATALYSIS, 2019, 9 (08) :7335-7342
[32]   Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction [J].
Qiao, Jin-Bao ;
Zhang, Ya-Qian ;
Yao, Qi-Wei ;
Zhao, Zhen-Zhen ;
Peng, Xuejing ;
Shu, Xing-Zhong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (33) :12961-12967
[33]   Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines [J].
Qin, Xurong ;
Lee, Marcus Wen Yao ;
Zhou, Jianrong Steve .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (41) :12723-12726
[34]   Recent Advances in Nickel Catalysis Enabled by Stoichiometric Metallic Reducing Agents [J].
Richmond, Edward ;
Moran, Joseph .
SYNTHESIS-STUTTGART, 2018, 50 (03) :499-513
[35]   Enantioselective methodologies for the synthesis of spiro compounds [J].
Rios, Ramon .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1060-1074
[36]   Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes [J].
Sanford, Amberly B. ;
Thane, Taylor A. ;
McGinnis, Tristan M. ;
Chen, Pan-Pan ;
Hong, Xin ;
Jarvo, Elizabeth R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (11) :5017-5023
[37]   Spiro compounds for organic optoelectronics [J].
Saragi, Tobat P. I. ;
Spehr, Till ;
Siebert, Achim ;
Fuhrmann-Lieker, Thomas ;
Salbeck, Josef .
CHEMICAL REVIEWS, 2007, 107 (04) :1011-1065
[38]   SPIROCONJUGATION [J].
SIMMONS, HE ;
FUKUNAGA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) :5208-&
[39]   Recent advances in homogeneous nickel catalysis [J].
Tasker, Sarah Z. ;
Standley, Eric A. ;
Jamison, Timothy F. .
NATURE, 2014, 509 (7500) :299-309
[40]   Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes [J].
Tian, Zhi-Xiong ;
Qiao, Jin-Bao ;
Xu, Guang-Li ;
Pang, Xiaobo ;
Qi, Liangliang ;
Ma, Wei-Yuan ;
Zhao, Zhen-Zhen ;
Duan, Jicheng ;
Du, Yun-Fei ;
Su, Peifeng ;
Liu, Xue-Yuan ;
Shu, Xing-Zhong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (18) :7637-7643