CHIRAL TOLUENE-2,α-SULTAM AUXILIARIES: ASYMMETRIC ALKYLATIONS, ACYLATIONS AND ALDOLIZATIONS OF N-ACYL DERIVATIVES

DOI: 10.1016/S0040-4039(00)97794-3

Source and publish data:

Tetrahedron Letters p. 5019 - 5022 (1990)

Update date:2022-07-29

Topics:

Authors:

Oppolzer, Wolfgang

Rodriguez, Ines

Starkemann, Christian

Walther, Eric

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

Article abstract of DOI:10.1016/S0040-4039(00)97794-3

Successive treatment of (R)-N-acylsultams 4 with NHDMS/alkyl halides or NHDMS/acyl chlorides provides alkylated or acylated products 6 or 7.Diastereoselective reductions of 7 with Zn(BH4)2 or NaHB(sBu)3 gives "syn"- or "anti"-aldols 8 or 9.Reaction of 4 with BEt3/TfOH/EtN(iPr)2 followed by addition of aromatic or aliphatic aldehydes affords diastereomerically pure "syn"-aldols 10.Non-destructive removal of auxiliary 3 from 6, 8, 9 and 10 yields enantiomerically pure products 12 to 16.

Full text of DOI:10.1016/S0040-4039(00)97794-3

Products guided by the article

Product name:(R)-2-Methyl-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-3-phenyl-propan-1-one

Cas No:131700-95-3

R&D Labs maybe for 131700-95-3

Jiangsu Mingchem Corporation

website:http://www.mingchem.com/en/index

Contact:0519-85170101-802

Address:Fifth Floor,B of Beihua Buliding,520 Road of Science and Education City,Changwu middle road NO.801,Wujin District,Changzhou,Jiangsu province
Nanjing Fubang Chemical Co.,Ltd

Contact:+86-25-83179199

Address:5F,Tianzheng international plaza,No399 Zhongyang Road ,Nanjing China
Shanghai Mintchem Development ., Ltd

Contact:0086 21 5190 8570

Address:R602,4#,89Nong, Mudan Road Pudong Shanghai China
Shanghai Bosman Industrial Co., Ltd

Contact:86-21-63065878-8006

Address:Rm907, No.1611, North Sichuan Road, Hongkou District, Shanghai, 200080 China
Chinese Peptide Company

Contact:86-571-86737118-8689

Address:No.69, 12 Street, HEDA, Hangzhou, Zhejiang, China

Relevant to this article

Design, synthesis and biological assessment of novel N-substituted 3-(phthalimidin-2-yl)-2,6-dioxopiperidines and 3-substituted 2,6-dioxopiperidines for TNF-α inhibitory activity

Doi:10.1016/j.bmc.2011.05.029
(2011)
Synthesis and biological evaluation of novel 5-alkyl-2-arylthio-6-((3,4- dihydroquinolin-1(2H)-yl)methyl)pyrimidin-4(3H)-ones as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

Doi:10.1016/j.bmc.2011.05.024
(2011)
Palladium(II)-catalyzed direct intermolecular alkenylation of chromones

Doi:10.1021/ol2018278
(2011)
SYNTHESIS AND VASCULAR ACTIVITY EXAMINATION OF 3-DIMETHOXYPHOSPHORYL PROPYL ESTERS OF N-ACYL DERIVATIVES OF NEUROACTIVE MONOCARBOXYLIC AMINO ACIDS

Doi:10.1007/BF00766546
(1990)
Studies in Sugar Chemistry. 2. A Simple Method for O-Deacylation of Polyacylated Sugars

Doi:10.1021/jo00355a026
(1986)
Inhibition of nonmammalian glycosidases by azetidine iminosugars derived from stable 3,5-Di-O-triflates of pentoses

Doi:10.1021/ol2024482
(2011)

Article Doi