Diastereoselective α Allylation of Secondary and Tertiary Thioamides via Thio-Claisen Rearrangement. A Structural Proof of Z Secondary Thioamide Dianions and Z Tertiary Thioamide Anions

DOI: 10.1021/jo00169a003

Source and publish data:

Journal of Organic Chemistry p. 3631 - 3639 (1983)

Update date:2022-08-04

Topics:

Authors:

Tamaru, Y.

Furukawa, Y.

Mizutani, M.

Kitao, O.

Yoshida, Z.

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

Article abstract of DOI:10.1021/jo00169a003

Highly diastereoselective α allylation of secondary and tertiary thioamides is achieved by making use of thio-Claisen rearrangement.From the correlation between the diastereoselectivities in products and the structures of allylating agents, the Z structures of secondary thioamide dianion (ca. 100percent Z) and tertiary thioamide anion (>97percent Z) are concluded.

Full text of DOI:10.1021/jo00169a003

Products guided by the article

Product name:threo-N-methyl-3-(1-phenyl-2-propenyl)pyrrolidine-2-thione

Cas No:86943-16-0

R&D Labs maybe for 86943-16-0

Phantom-pharma

Contact:

Address:
Changsha Yonta Industry Co., Ltd.

Contact:+ 86-731-8535 2228

Address:Rm.1717, North Bldg., No.368, East 2nd Ring Road(2nd Section)
Shaanxi WuZhiYuan Biological Technology Co.,Ltd

Contact:+86 18791979989

Address:No24.west fengming road,fengming town,qishan county
jiangsu hualin chemical co.,ltd.

Contact:86-25-87787402

Address:jaingsu,china
SAGECHEM LIMITED

website:http://www.sagechem.com

Contact:+86-571-86818502

Address:Room C1301, New Youth Plaza, 8 Jia Shan Road, Hangzhou, China

Relevant to this article

The reaction of 6-phenylthiouridine with sulfur nucleophiles: A simple and regiospecific preparation of 6-alkylthiouridines and 6-alkylthiouridylic acids

Doi:10.1248/cpb.31.1222
(1983)
2-Amino-1,3-thiazol-4(5H)-ones as potent and selective 11β- hydroxysteroid dehydrogenase type 1 inhibitors: Enzyme-ligand co-crystal structure and demonstration of pharmacodynamic effects in C57Bl/6 mice

Doi:10.1021/jm701551j
(2008)
Tautomerization of methyldiazene to formaldehyde-hydrazone in ruthenium and osmium complexes

Doi:10.1021/ic050817z
(2005)
Indium-mediated alkyl radical addition to (η⁶-arene) tricarbonylmanganese complexes in aqueous media

Doi:10.1021/om050721c
(2005)
Regulation of saccharide binding with basic poly(ethynylpyridine)s by H⁺-induced helix formation

Doi:10.1021/ja054134u
(2005)
Synthesis of a linear benzo[3]phenylene-[60]fullerene dyad

Doi:10.1016/j.tetlet.2005.09.174
(2005)

Article Doi