High 1,6 diastereoselectivity in the hydride reduction of an acyclic ketone substrate via bicyclic chelation control

DOI: 10.1016/0040-4039(96)01767-4

Source and publish data:

Tetrahedron Letters p. 7897 - 7900 (1996)

Update date:2022-08-03

Topics:

Authors:

Zhang, Han-Cheng

Harris, Bruce D.

Maryanoff, Cynthia A.

Maryanoff, Bruce E.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/0040-4039(96)01767-4

Reduction of acyclic ε-hydroxy ketone 3 with R-Alpine-Hydride in methylene chloride provided a strong preponderance of the anti diasteromer of 4 (anti:syn = 12:1). This impressive 1,6 stereoselectivity is attributed to bicyclic chelation control of hydride addition.

Full text of DOI:10.1016/0040-4039(96)01767-4

Products guided by the article

Product name:1-Propanone, 3-[(2-methoxy-2-phenylethyl)(phenylmethyl)amino]-1-phenyl-

Cas No:185376-72-1

R&D Labs maybe for 185376-72-1

Heading（Nanjing）Pharmtechnologies

Contact:86 25 58467899-950 025-58862846-950

Address:Room C413 Fengyu Building, 115 Fucheng Road, Haidian District, Beijing 100142, China
Chongqing Yawei Fine Chemical Co.,Ltd

Contact:0086-23-62849407

Address:Ziyou village, Nanquan town, Banan district, Chongqing China
ABA Chemicals (Shanghai) Limited

Contact:021- 5115 9199-232

Address:Suite 18D, #201 Ningxia Road,
Shanghai Forxine Pharmaceutical Co., Ltd.

Contact:86-021-64961699

Address:1835, Duhui Road, Minhang District, Shanghai/ 201108/ P.R. China
Yingkou Sanzheng Organic Chemical Co. Ltd.

Contact:+86-417-3638818

Address:25 Gengxinli Village, Daqing Road, Yingkou, Liaoning, China

Relevant to this article

Lead discovery, chemistry optimization, and biological evaluation studies of novel biamide derivatives as CB₂ receptor inverse agonists and osteoclast inhibitors

Doi:10.1021/jm301212u
(2012)
Doi:10.1007/BF00901092
(1967)
Optimisation of BACE1 inhibition of tripartite structures by modification of membrane anchors, spacers and pharmacophores - Development of potential agents for the treatment of Alzheimer's disease

Doi:10.1039/c2ob26103k
(2012)
Novel cyanocombretastatins as potent tubulin polymerisation inhibitors

Doi:10.1016/j.bmcl.2012.08.089
(2012)
Copper-catalyzed synthesis of N-aryl acridones from 2-amino benzophenones and aryl boronic acids via sequential double oxidative C–N coupling

Doi:10.1002/aoc.5316
(2020)
Utilization of O-xylylene N,N-diethylphosphoramidite for the synthesis of phosphoric diesters

Doi:10.1016/S0040-4039(00)91610-1
(1992)

Article Doi