Literature DB >> 12517138

A direct catalytic asymmetric mannich-type reaction to syn-amino alcohols.

Barry M Trost1, Lamont R Terrell.   

Abstract

The Mannich reaction is one of the most widely utilized chemical transformations for the construction of nitrogen-containing compounds. With the increasing occurrence of nitrogen in drugs and natural products, highly asymmetric variants of the Mannich reaction are desirable. In this communication, we report the application of our dinuclear zinc catalyst to a highly asymmetric Mannich-type reaction to generate syn 1,2-amino alcohols.

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Year:  2003        PMID： 12517138     DOI： 10.1021/ja028782e

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


  19 in total

Review 1.  Asymmetric catalysis: an enabling science.

Authors:  Barry M Trost
Journal:  Proc Natl Acad Sci U S A       Date:  2004-02-27       Impact factor: 11.205

2.  Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.

Authors:  Barry M Trost; Andrew H Weiss; Axel Jacobi von Wangelin
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

3.  Direct asymmetric anti-Mannich-type reactions catalyzed by a designed amino acid.

Authors:  Susumu Mitsumori; Haile Zhang; Paul Ha-Yeon Cheong; K N Houk; Fujie Tanaka; Carlos F Barbas
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

4.  syn-1,2-Amino alcohols via diastereoselective allylic C-H amination.

Authors:  Kenneth J Fraunhoffer; M Christina White
Journal:  J Am Chem Soc       Date:  2007-05-22       Impact factor: 15.419

5.  Direct asymmetric Zn-aldol reaction of methyl vinyl ketone and its synthetic applications.

Authors:  Barry M Trost; Seunghoon Shin; Joseph A Sclafani
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

6.  Practical and highly enantioselective synthesis of beta-alkynyl-beta-amino esters through Ag-catalyzed asymmetric mannich reactions of silylketene acetals and alkynyl imines.

Authors:  Nathan S Josephsohn; Emma L Carswell; Marc L Snapper; Amir H Hoveyda
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

7.  A direct catalytic asymmetric Mannich-type reaction via a dinuclear zinc catalyst: synthesis of either anti- or syn-alpha-hydroxy-beta-amino ketones.

Authors:  Barry M Trost; Jaray Jaratjaroonphong; Vichai Reutrakul
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

8.  Accelerated C-N bond formation in dropcast thin films on ambient surfaces.

Authors:  Abraham K Badu-Tawiah; Dahlia I Campbell; R Graham Cooks
Journal:  J Am Soc Mass Spectrom       Date:  2012-07-24       Impact factor: 3.109

9.  Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

Authors:  Barry M Trost; Mark J Bartlett; Andrew H Weiss; Axel Jacobi von Wangelin; Vincent S Chan
Journal:  Chemistry       Date:  2012-10-23       Impact factor: 5.236

10.  Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: a powerful entry into chiral building blocks.

Authors:  Barry M Trost; Sushant Malhotra; Takashi Mino; Naomi S Rajapaksa
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
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