Beilstein Journal of Organic Chemistry p. 1870 - 1876 (2016)
Update date:2022-08-04
Topics: Synthesis Chiral Analog Structure Catalysis Bicyclic guanidine TBD Br?nsted base
Goldberg, Mariano
Sartakov, Denis
Bats, Jan W.
Bolte, Michael
G?bel, Michael W.
Starting from (S)-β-phenylalanine, easily accessible by lipase-catalyzed kinetic resolution, a chiral triamine was assembled by a reductive amination and finally cyclized to form the title compound 10. In the crystals of the guanidinium benzoate salt the six membered rings of 10 adopt conformations close to an envelope with the phenyl substituents in pseudo-axial positions. The unprotonated guanidine 10 catalyzes Diels-Alder reactions of anthrones and maleimides (25-30% ee). It also promotes as a strong Br?nsted base the retro-aldol reaction of some cycloadducts with kinetic resolution of the enantiomers. In three cases, the retroaldol products (48-83% ee) could be recrystallized to high enantiopurity (≥95% ee). The absolute configuration of several compounds is supported by anomalous X-ray diffraction and by chemical correlation.
View MoreJIANGSU GRAND XINYI PHARMACEUTICAL CO.,LTD
website:http://www.xypharm.com/
Contact:+86-515-84383317
Address:Chenli Road,Costal Chemical Area Binhai,Yancheng, Jiangsu,China
Chengdu NoVi Biotechnology Co., Ltd.
Contact:13551243286/028-81458053
Address:NO.168-1-224 JULONG ROAD WUHOU DISTRICT, CHENGDU CITY,SICHUAN PROVINCE
Shanghai Mio Chemical Co., Ltd
Contact:0086 21- 64401188-622
Address:16 Floor NO.2 Jiefang Building, No. 4855 Dushi Road, 201100 Shanghai, P.R.China
Shuanghe Bio-Technology Limited
Contact:+86-571-61710758,18968016640
Address:Jinqiao north road 916# Fuyang
hangzhou verychem science and technology co.ltd
website:http://www.verypharm.com
Contact:+86-571-88162785; 88162786
Address:F1502, 753 Shenhua road, Hangzhou, China
Doi:10.1016/0040-4039(94)02488-W
(1995)Doi:10.1006/bioo.1995.1006
(1995)Doi:10.1080/15533170903433220
(2009)Doi:10.1002/anie.201405023
()Doi:10.3184/174751914X14019525018744
(2014)Doi:10.1007/s12039-014-0633-9
(2014)