Literature DB >> 16011341

A simple and general chiral silicon Lewis acid for asymmetric synthesis: highly enantioselective [3+2] acylhydrazone-enol ether cycloadditions.

Seiji Shirakawa1, Pamela J Lombardi, James L Leighton.   

Abstract

A highly diastereo- and enantioselective [3 + 2] acylhydrazone-enol ether cycloaddition mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the product was obtained after recrystallization in 93% yield and 99% ee. Evidence for a stepwise mechanism and a model for the asymmetric induction are presented, as well.

Entities:  

Year:  2005        PMID： 16011341     DOI： 10.1021/ja052307+

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Highly stereoselective formal [3 + 3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes.

Authors:  Audrey Chan; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-04-04       Impact factor: 15.419

2.  Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Authors:  Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; Hongchao Guo; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2011-08-03       Impact factor: 15.419

3.  Highly enantioselective Mannich reactions with α-aryl silyl ketene acetals and imines.

Authors:  Gregory T Notte; Jenny M Baxter Vu; James L Leighton
Journal:  Org Lett       Date:  2011-01-14       Impact factor: 6.005

4.  Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates.

Authors:  Chengfeng Jing; Risong Na; Bo Wang; Honglei Liu; Lei Zhang; Jun Liu; Min Wang; Jiangchun Zhong; Ohyun Kwon; Hongchao Guo
Journal:  Adv Synth Catal       Date:  2012-04-26       Impact factor: 5.837

5.  Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.

Authors:  Uttam K Tambar; Sharon K Lee; James L Leighton
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

6.  Convenient access to bicyclic and tricyclic diazenes.

Authors:  Douglass F Taber; Pengfei Guo
Journal:  J Org Chem       Date:  2008-12-05       Impact factor: 4.354

7.  Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via Pd-catalyzed carboamination reactions: use of allylic strain to control product stereochemistry through N-substituent manipulation.

Authors:  Natalie C Giampietro; John P Wolfe
Journal:  J Am Chem Soc       Date:  2008-09-06       Impact factor: 15.419

Review 8.  Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines.

Authors:  Franc Požgan; Hamad Al Mamari; Uroš Grošelj; Jurij Svete; Bogdan Štefane
Journal:  Molecules       Date:  2017-12-21       Impact factor: 4.411

9.  Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives.

Authors:  Zhi-Cong Geng; Jian Chen; Ning Li; Xiao-Fei Huang; Yong Zhang; Ya-Wen Zhang; Xing-Wang Wang
Journal:  Beilstein J Org Chem       Date:  2012-10-09       Impact factor: 2.883

10.  Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides.

Authors:  Lena Hesping; Anup Biswas; Constantin G Daniliuc; Christian Mück-Lichtenfeld; Armido Studer
Journal:  Chem Sci       Date:  2014-11-19       Impact factor: 9.825
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.