Journal of Organic Chemistry p. 1112 - 1119 (1991)
Update date:2022-08-03
Topics:
Yamamoto, Yukio
Sakamoto, Akio
Nishioka, Takaaki
Oda, Jun'ichi
Fukazawa, Yoshimasa
Optically active lactones were synthesized by a novel asymmetric synthesis in which enantiotopic groups remote from a prochiral center were effectively discriminated.The cyclic diamide alcohols bearing a C2-chiral auxiliary, (+)-<1,1'-binaphthyl>-2,2'-diamine (4), were designed and prepared such that the hydroxyl group should attack preferentially at one of the two carbonyl groups.By the catalytic action of trifluoroacetic acid, the substrates 6a,b and 19 were smoothly converted to the lactones 7a (71percent de), 7b (97percent de), and 20 (>99percent de), the configurations of whichwere determined to be R, S, and R, respectively.A naturally occurring pheromone, (R)-(+)-5-hexadecanolide (13), was synthesized optically pure from 7b.Transition-state models for the present asymmetric lactonization were constructed according to the stereoelectronic theory proposed by Deslongchamps.The stability of the models was assessed by MM2 calculation, and the direction of asymmetric induction thus calculated coincided with the experimental results.
View MoreBAODING SINO-CHEM INDUSTRY CO.,LTD
Contact:0312-5956088
Address:NO.8 FUXING ROAD,CHINA
Shenyang Xinyihan Chemical Technology Co., Ltd.
Contact:+86-18525026267
Address:362, aigongbeijei street 23 , tiexi district,Shenyang, Liaoning, China
FUJIAN SHANSHUI CHEMICAL CORP.LTD.
Contact:+86-151-59920036
Address:Jinqiao Gareden, jo@fj-xinyi.com
Ningbo Distant Chemicals Co.,Ltd
Contact:86-574-27862490,27862438
Address:5F-3,#54 DaShaNi street,Ningbo,CHINA
Contact:+86-25-52346955
Address:199,JIANYE ROAD,NANJING,CHINA
Doi:10.1155/2011/723421
(2011)Doi:10.1016/j.apcata.2015.05.003
(2015)Doi:10.1039/c39900000911
(1990)Doi:10.1016/0957-4166(90)80010-V
(1990)Doi:10.1016/0223-5234(90)90188-9
(1990)Doi:10.1021/ol201705k
(2011)