Rational design and atroposelective synthesis of N-N axially chiral compounds

被引:119
作者
Mei, Guang-Jian [1 ,2 ,3 ]
Wong, Jonathan J. [4 ]
Zheng, Wenrui [3 ]
Nangia, Anjanay A. [4 ]
Houk, K. N. [4 ]
Lu, Yixin [3 ,5 ]
机构
[1] Zhengzhou Univ, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China
[2] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
[3] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore
[4] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[5] Tianjin Univ, Joint Sch Natl Univ Singapore & Tianjin Univ, Int Campus, Fuzhou 350207, Fujian, Peoples R China
基金
新加坡国家研究基金会;
关键词
ENANTIOSELECTIVE SYNTHESIS; NATURAL-PRODUCTS; RESOLUTION; ATROPISOMERISM; CONSTRUCTION; DERIVATIVES; CYCLIZATION; HYDRAZINES; AMINATION; LIGANDS;
D O I
10.1016/j.chempr.2021.07.013
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first catalytic asymmetric synthesis of N-N axially chiral compounds has been accomplished via a quinidine catalyzed N-allylic alkylation reaction. These N-N axially chiral frameworks are a new addition to the families of axially chiral molecules and to the atropisomerism involving heteroatom(s), e.g., N, O, and S. The reaction takes place smoothly under mild conditions and displays excellent functional group tolerance, allowing facile access to a variety of N-N axially chiral 1-aminopyrroles and 3-aminoquinazolinones in high yields and excellent enantioselectivities. DFT calculations have been applied to understand the origin of enantioselectivity and provide guidance for the design of additional molecules of this type. The investigation of N-N axis atropisomerism holds promise for new discoveries in medicinal chemistry and asymmetric catalysis.
引用
收藏
页码:2743 / 2757
页数:15
相关论文
共 82 条
[1]   The stereochemistry of diphenyls and analogous compounds [J].
Adams, R ;
Yuan, HC .
CHEMICAL REVIEWS, 1933, 12 (02) :261-338
[2]   Synthesis of Enantiopure Isosteres of Amino Acids Containing a Quaternary Stereocenter: Experimental and Computational Evaluation of a Novel Class of Atropisomers [J].
Amabili, Paolo ;
Amici, Adolfo ;
Campisi, Giovanni ;
Guerra, Giulia ;
Monari, Magda ;
Orena, Mario ;
Piccinelli, Fabio ;
Rinaldi, Samuele ;
Tolomelli, Alessandra .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (46) :6524-6536
[3]   Highly stable atropisomers by electrophilic amination of a chiral γ-lactam within the synthesis of an elusive conformationally restricted analogue of α-methylhomoserine [J].
Amabili, Paolo ;
Amici, Adolfo ;
Civitavecchia, Annafelicia ;
Maggiore, Beatrice ;
Orena, Mario ;
Rinaldi, Samuele ;
Tolomelli, Alessandra .
AMINO ACIDS, 2016, 48 (02) :461-478
[4]  
Antognazza P, 1999, PHOSPHORUS SULFUR, V144, P405, DOI 10.1080/10426509908039582
[5]   Straightforward entry into 5-hydroxy-1-aminopyrrolines and the corresponding pyrroles from 1,2-diaza-1,3-butadienes [J].
Attanasi, OA ;
De Crescentini, L ;
Favi, G ;
Filippone, P ;
Mantellini, F ;
Santeusanio, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (23) :8178-8181
[6]   Synthesis of new cycloalkenyliden-pyrroles by domino reaction [J].
Attanasi, Orazio A. ;
Berretta, Stefano ;
De Crescentini, Lucia ;
Favi, Gianfranco ;
Golobic, Amalija ;
Mantellini, Fabio .
TETRAHEDRON, 2009, 65 (11) :2290-2297
[7]   Enantioselective Synthesis of Atropisomers with Multiple Stereogenic Axes [J].
Bao, Xiaoze ;
Rodriguez, Jean ;
Bonne, Damien .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (31) :12623-12634
[8]   Spontaneous transfer of chirality in an atropisomerically enriched two-axis system [J].
Barrett, Kimberly T. ;
Metrano, Anthony J. ;
Rablen, Paul R. ;
Miller, Scott J. .
NATURE, 2014, 509 (7498) :71-75
[9]   Enantioselective Synthesis of Atropisomeric Benzamides through Peptide-Catalyzed Bromination [J].
Barrett, Kimberly T. ;
Miller, Scott J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (08) :2963-2966
[10]   Chiral atropisomeric five-membered biheteroaromatic diphosphines: New ligands of the bibenzimidazole and biindole series [J].
Benincori, T ;
Brenna, E ;
Sannicolo, F ;
Trimarco, L ;
Antognazza, P ;
Cesarotti, E ;
Demartin, F ;
Pilati, T ;
Zotti, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 529 (1-2) :445-453