Journal of Organic Chemistry p. 7674 - 7692 (2015)
Update date:2022-08-15
Topics: -Synthesis -Intramolecular cyclization -Enantiopure -3-Hydroxypiperidines -Sulfinyl Dienyl Amines -Diastereoselective -[2,3]-Sigmatropic Rearrangement
Simal, Carmen
Bates, Robert H.
Urena, Mercedes
Giménez, Irene
Koutsou, Christina
Infantes, Lourdes
Fernández De La Pradilla, Roberto
Viso, Alma
The highly diastereoselective base-promoted intramolecular cyclization of a variety of enantiopure sulfinyl dienyl amines provides novel sulfinyl tetrahydropyridines that are readily converted to 3-hydroxy tetrahydropyridines via sigmatropic rearrangement. The influence of N- and C- substituents on the process has been studied. Procedures to shorten the sequence such as the tandem cyclization followed by [2,3]-sigmatropic rearrangement, as well as cyclization of the free amine, under Boc- or ArSO- deprotection conditions have been examined. Good to excellent levels of selectivity are generally observed for the reported transformations (dr: 75/25 to >98/2). A novel protocol to access substituted amino dienyl sulfoxides is also reported.
View MoreHANGZHOU TOYOND BIOTECH CO., LTD
Contact:+86-571-86965177
Address:No. 189, Fengqi East Road, Hangzhou, China
Henan Yellow River New Material Technology Co.Ltd.
website:http://www.yellowriverchem.com
Contact:0086-373-7278760
Address:Chengguan Town, Yuanyang County
Shanghai Potomer International Trade CO., LTD
Contact:+86-21-61397128
Address:Room 304,No.505 ,Caoyang Road.Shanghai,China
Geen Chemical Technology Co., Ltd
Contact:86-769-21660847
Address:1408, Yingfeng Commercial Center, Nancheng District
Yancheng Creator Chemical Co., Ltd
Contact:0086-515-88710008 88710068 88710858 88710868
Address:No.21 Renming Road, Longgang Town, Yandu County,Yancheng City
Doi:10.1246/bcsj.59.1587
(1986)Doi:10.1021/ol102170q
(2010)Doi:10.1248/cpb.33.4564
(1985)Doi:10.1248/cpb.34.2900
(1986)Doi:10.1021/jm00384a019
(1987)Doi:10.1016/j.steroids.2013.03.004
(2013)