Chiral Induction in Aryl Radical Cyclization to the Aldimino Functional Group

DOI: 10.1039/c39930000966

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 966 - 968 (1993)

Update date:2022-07-29

Topics:

Authors:

Tomaszewski, Miroslaw J.

Warkentin, John

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

Article abstract of DOI:10.1039/c39930000966

6-endo Cyclization of aryl radicals to carbon of aldimino double bonds (N-5/C-6) in chiral ortho-substituents afforded 1,2,3,4-tetrahydroisoquinolines in yields to 69percent, with 58percent d.e. and 97percent e.e., while 5-exo cyclization to carbon in isomeric radicals (C-5/N-6 aldimine), leading to indanamines, was highly regioselective and fast, k_5-exo = 3.9 * 10⁸ s^-1 at 80 deg C.

Full text of DOI:10.1039/c39930000966

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:(S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester

Cas No:164020-75-1

R&D Labs maybe for 164020-75-1

Lianyungang Ningkang Chemical Co., Ltd

Contact:.+86-518-88588008

Address:http://www.chemnk.com
Daicel Chiral Technologies (China)CO.,LTD

Contact:021-5046-0086*8

Address:Part C, FL 5, the 16th Building, No. 69, XiYa Road, WaiGaoQiao Free Trade Zone, Shanghai, 200131, P.R.China
Hangzhou Taiyan Trading Co., Ltd(expird)

Contact:+86-13777583958

Address:NO.63, Xingyi Street, Xihu District, Hangzhou, Zhejiang, China
Wuxi Pharma-Trading Import & Export Co.,Ltd.

Contact:+86-510-82304590 82716390

Address:Room 523,Youzu Alliance Building,No.88 Renmin Zhonglu,Wuxi,Jiangsu,China
Shijiazhuang Yunxuan Im&Export Co.,Ltd.

Contact:+86-311-83037514

Address:No.6 Hongbin Road

Relevant to this article

Structure-assisted functional anchor implantation in robust metal-organic frameworks with ultralarge pores

Doi:10.1021/ja5123528
(2015)
Design, Synthesis, and Preclinical Characterization of Selective Factor D Inhibitors Targeting the Alternative Complement Pathway

Doi:10.1021/acs.jmedchem.9b00271
(2019)
Stereoselective synthesis of rare (D and L) mono and disaccharides of 5-deoxy hexofuranosiduronic acids by a facile intramolecular rearrangement of hemiacetal heptanolactone alcohols

Doi:10.1016/0040-4020(94)01047-4
(1995)
Synthesis of Silver(I) Complexes with 1,1'-Bis(diphenylphosphino)ferrocene (dppf). Crystal Structures of ClO4*2CH2Cl2, ClO4*2CHCl3 and ClO4 (phen = 1,10-phenanthroline)

Doi:10.1039/DT9950001473
(1995)
Thermodynamics and selectivity of complexation of lithium and sodium thiocyanates with phosphorus-containing podands and compounds modeling the terminal groups of these podands

Doi:10.1007/BF00697134
(1994)
1,3-Stereocontrol with bromoallenes. Synthesis of N-Boc-ADDA, the unique amino acid present in several inhibitors of serine/threonine phosphatases

Doi:10.1021/jo9605004
(1996)

Article Doi