Nitrone Cycloaddition in the Stereoselective Synthesis of β-Carbolines from N-Hydroxytryptophan

DOI: 10.1021/jo00353a007

Source and publish data:

Journal of Organic Chemistry p. 309 - 314 (1986)

Update date:2022-09-26

Topics:

Authors:

Plate, Ralf

Hermkens, Pedro H. H.

Smits, Jan M. M.

Ottenheijm, Harry C. J.

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

Article abstract of DOI:10.1021/jo00353a007

The cycloaddition chemistry of nitrone 6, obtained by treatment of N-hydroxytryptophan ester 4 with methyl orthoformate, has been evaluated. 1,3-Dipolar cycloadditions with alkenes proceed with high or complete regioselectivity to yield 4'- or 5'-substituted isoxazolidines (Scheme II).Complete C(3) C(1) trans induction as well as high or complete stereoselectivity at the other newly introduced chiral center C(4') or C(5') is observed.The regiochemical course of these reactions is as predicted by frontier molecular orbital theory.

Full text of DOI:10.1021/jo00353a007

Products guided by the article

Product name:(exo)-2-phenyl-5-ethoxycarbonyl-4,5,6,11b-tetrahydroisoxazolidino-<2,3-a>-β-carboline

Cas No:99708-10-8

R&D Labs maybe for 99708-10-8

Ceresking Ecology & Technology co.,ltd

Contact:86 22 66218397

Address:Room 1613, Zheshang Mansion, No. 1988, Yingbin Avenue, Binhai New District, Tianjin,China.
Watson International Ltd

Contact:+44 (0)2036089360-31

Address:Chanceryhouse,Chancery Lan
H&Y International Group Ltd

Contact:+86-571-86491666

Address:SHI XIANG ROAD
Changsha Botaniex Inc.

Contact:(86) 731 88718666

Address:Room 1222, Unit 4, Building B, Shangcheng, No.47, Kaiyuan East Road.
Hefei Highzone Fine Chemical S&T CO.,LTD

Contact:86-0551-63663560

Address:room 1801 NO. 24 Shuguang RD.

Relevant to this article

DBU and DBU-Derived Ionic Liquid Synergistic Catalysts for the Conversion of Carbon Dioxide/Carbon Disulfide to 3-Aryl-2-oxazolidinones/[1,3]Dithiolan-2-ylidenephenyl- Amine

Doi:10.1002/cctc.201500928
(2016)
Elimination processes for alkyl, hydride, and hydroxy derivatives of permethyltungstenocene

Doi:10.1021/om00107a008
(1989)
Facile Synthesis of Protected β,β-Dialkylcysteine Derivatives Suitable for Peptide Synthesis

Doi:10.1021/jo00254a044
(1988)
Doi:10.1021/ja01559a059
(1957)
Regioselective ring opening of thiomalic acid anhydrides by carbon nucleophiles. Synthesis and X-ray structure elucidation of novel thiophenone derivatives

Doi:10.1016/j.tet.2009.02.081
(2009)
Sterospecific Synthesis of (-)-Anisomycin from D-Galactose

Doi:10.1021/jo00255a022
(1988)

Article Doi