Liebigs Annalen p. 563 - 571 (1997)
Update date:2022-08-05
Topics:
Wilken, Joerg
Martens, Juergen
New, chiral β-sec-amino alcohols 3a-d, 4a-e, and 5a-h have been synthesized from the enantiomerically pure amine (all-R)-2a. For the diastereo- and regioselective α-hydroxyaklyation of the chiral (all-R)-N-nitroso-2-azabicyclo[3.3.0]octane (all-R)-2d, Seebach's "one pot" method was chosen. The versatile nucleophilic intermediate reacts regio-and stereoselectively with a variety of electrophiles to afford 3-substituted pyrrolidine derivatives, e.g. (erythro)-(αR,βS)-amino alcohol frameworks with four sterically crowded stereogenic centers, and (βS)-configured tricyclic structures with a cycloalkynol building block (see formulae 3a-d, 4a-e, and 5a-h). Alkylation products are obtained in fair yields with a high degree of stereoselectivity (diastereomeric ratios dr up to 93:7). A mechanistic interpretation of the stereochemical course of this reaction is presented. - This is a further example of the synthesis of interesting new chiral ligands from the industrial waste material (all-R)-2-azabicyclo[3.3.0]octane-3-carboxylic acid benzyl ester (all-R)-1a. The catalytic ability of selected (erythro)- and new, related stereoisomeric amino alcohol structures were tested in the enantioselective borane reduction using the prochiral acetophenone as model substrate (enantiomeric excesses ee up to 86%). VCH Verlagsgesellschaft mbH, 1997.
View MoreNanjing lanbai chemical Co.,Ltd.
Contact:+86-25-85499326
Address:Room 908, 9F Taiyue Building,No.285 Heyan Road
LINYI FUDE FINE CHEMICAL CO.,LTD
Contact:86-539-2361184
Address:YISHUI, LINYI,SAHNDONG,CHINA
Shanghai united Scientific Co.,Ltd.
Contact:+86-21-53535353
Address:28F No.900 huaihai Road Shanghai China
Hefei EnliPharma Tecnology Co.,Ltd
Contact:0086-551-66399836
Address:Qing Cheng ShuiXiang Building 805, Mengcheng North Road , ShuangFeng Economic Development Zone Anhui HeFei
BrightGene Bio-Medical Technology Co., Ltd.
website:https://en.bright-gene.com/
Contact:+86-512-62551801
Address:Building C25 - C31, No. 218 Xinghu Road, Suzhou Industrial Park, Suzhou, Jiangsu, China.
Doi:10.1007/s11164-015-2117-z
(2016)Doi:10.1021/ja972381v
(1997)Doi:10.1021/ja01644a034
(1954)Doi:10.1055/s-1997-999
(1997)Doi:10.1080/10610278.2016.1236197
(2017)Doi:10.1246/bcsj.41.1372
(1968)