Light-induced stereospecific intramolecular [2+2]-cycloaddition of atropisomeric 3,4-dihydro-2-pyridones

被引:22
作者
Kumarasamy, Elango [1 ]
Sivaguru, J. [1 ]
机构
[1] N Dakota State Univ, Dept Chem & Biochem, Fargo, ND 58108 USA
基金
美国国家科学基金会;
关键词
PHOTOCHEMICAL-REACTIONS; STEREOSELECTIVITY; CHIRALITY; AMIDES;
D O I
10.1039/c2cc37123e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Atropisomeric 3,4-dihydro-2-pyridones undergo stereospecific [2+2]-photocycloaddition in solution with high stereoselectivity (ee > 98% and de > 96%) in the product. The chiral transfer during phototransformation was rationalized based on the stability/reactivity of the biradical.
引用
收藏
页码:4346 / 4348
页数:3
相关论文
共 23 条
[1]   Synthesis of enantioenriched axially chiral anilides from atropisomerically enriched tartarate ortho-anilides [J].
Ates, A ;
Curran, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (21) :5130-5131
[2]   Enantiospecific Photochemical Norrish/Yang Type II Reaction of Nonbiaryl Atropchiral α-Oxoamides in Solution-Axial to Point Chirality Transfer [J].
Ayitou, Anoklase Jean-Luc ;
Jesuraj, Josepha L. ;
Barooah, Nilotpal ;
Ugrinov, Angel ;
Sivaguru, J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (32) :11314-+
[3]   Light-Induced Transfer of Molecular Chirality in Solution: Enantiospecific Photocyclization of Molecularly Chiral Acrylanilides [J].
Ayitou, Anoklase Jean-Luc ;
Sivaguru, J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (14) :5036-+
[4]  
Bach T, 2001, CHEM-EUR J, V7, P4512, DOI 10.1002/1521-3765(20011015)7:20<4512::AID-CHEM4512>3.0.CO
[5]  
2-H
[6]   Highly enantioselective intra- and intermolecular [2+2] photocycloaddition reactions of 2-quinolones mediated by a chiral lactam host: Host-guest interactions, product configuration, and the origin of the stereoselectivity in solution [J].
Bach, T ;
Bergmann, H ;
Grosch, B ;
Harms, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7982-7990
[7]   Atropisomers and near-atropisomers: achieving stereoselectivity by exploiting the conformational preferences of aromatic amides [J].
Clayden, J .
CHEMICAL COMMUNICATIONS, 2004, (02) :127-135
[8]   Total synthesis of the putative structure of the lupin alkaloid plumerinine [J].
Comins, DL ;
Zheng, XL ;
Goehring, RR .
ORGANIC LETTERS, 2002, 4 (09) :1611-1613
[9]   The ionic auxiliary concept in solid state organic photochemistry [J].
Gamlin, JN ;
Jones, R ;
Leibovitch, M ;
Patrick, B ;
Scheffer, JR ;
Trotter, J .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (04) :203-209
[10]   Engineering carbene rearrangements in crystals: From molecular information to solid-state reactivity [J].
Garcia-Garibay, MA .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (07) :491-498