Enantioselective Synthesis of Axially Chiral Styrene-Carboxylic Esters by Rhodium-Catalyzed Chelation-Controlled [2+2+2] Cycloaddition

被引:36
作者
Yokose, Daisuke [1 ]
Nagashima, Yuki [1 ]
Kinoshita, Suzuka [1 ]
Nogami, Juntaro [1 ]
Tanaka, Ken [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Meguro Ku, Tokyo 1528550, Japan
关键词
Asymmetric Catalysis; Axial Chi rality; Cycloaddition; Rhodium; Styrenes; ASYMMETRIC-SYNTHESIS; ATROPOSELECTIVE SYNTHESIS; ATROPISOMERS; CONSTRUCTION; CONVERSION; RESOLUTION; LIGANDS; OLEFINS; ACIDS;
D O I
10.1002/anie.202202542
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Axially chiral styrene-carboxylic esters were synthesized in high yields with excellent enantioselectivity by the cationic rhodium(I)/H-8-BINAP complex-catalyzed chelation-controlled [2+2+2] cycloaddition reactions of 1,6- and 1,7-diynes with 1,3-enyne-carboxylic esters. The diastereo- and enantioselective synthesis of C-2 symmetric axially chiral cis and trans-stilbenedicarboxylic esters was also achieved by the double [2+2+2] cycloaddition reactions of two molecules of the 1,6-diyne with 2,3-dialkynylmaleate and 2,3-dialkynylfumarate, respectively. In these reactions, the 1,3-enynecarboxylic esters coordinating to rhodium with a five-membered chelate were more reactive than those coordinating to rhodium with a six-membered chelate, although both chelation modes realized excellent enantioselectivity. The enantioselection mechanism of the cationic rho dium(I)-catalyze d chelation-controlled [2+2+2] cycloaddition was elucidated by DFT calculations.
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页数:8
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