Literature DB >> 15281748

Asymmetric allylboration of aldehydes and ketones using 3,3'-disubstitutedbinaphthol-modified boronates.

T Robert Wu1, Lixin Shen, J Michael Chong.   

Abstract

Allylboronates derived from 3,3'-disubstituted 2,2'-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness. [reaction: see text]

Entities:  

Year:  2004        PMID： 15281748     DOI： 10.1021/ol0490882

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  21 in total

1.  Enantioselective conjugate allylation of cyclic enones.

Authors:  Douglass F Taber; David A Gerstenhaber; James F Berry
Journal:  J Org Chem       Date:  2011-08-23       Impact factor: 4.354

2.  Nonracemic 3 degrees-carbamines from the asymmetric allylboration of N-trimethylsilyl ketimines with B-allyl-10-phenyl-9-borabicyclo[3.3.2]decanes.

Authors:  Eda Canales; Eliud Hernandez; John A Soderquist
Journal:  J Am Chem Soc       Date:  2006-07-12       Impact factor: 15.419

3.  Origins of stereoselectivities in chiral phosphoric acid catalyzed allylborations and propargylations of aldehydes.

Authors:  Hao Wang; Pankaj Jain; Jon C Antilla; K N Houk
Journal:  J Org Chem       Date:  2013-01-18       Impact factor: 4.354

4.  A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides.

Authors:  Hiroyuki Morimoto; Tetsu Tsubogo; Nichole D Litvinas; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-25       Impact factor: 15.336

5.  Enantioselective synthesis of tryptophan derivatives by a tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction.

Authors:  Madeleine E Kieffer; Lindsay M Repka; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2012-03-05       Impact factor: 15.419

6.  Chiral Brønsted acid-catalyzed allylboration of aldehydes.

Authors:  Pankaj Jain; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

7.  Asymmetric synthesis of 2 degrees- and 3 degrees-Carbinols via B-methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes.

Authors:  José G Roman; John A Soderquist
Journal:  J Org Chem       Date:  2007-11-14       Impact factor: 4.354

8.  Molybdenum Imido Alkylidene Metathesis Catalysts that Contain Electron Withdrawing Biphenolates or Binaphtholates.

Authors:  Rojendra Singh; Constantin Czekelius; Richard R Schrock; Peter Müller; Amir H Hoveyda
Journal:  Organometallics       Date:  2007       Impact factor: 3.876

9.  Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.

Authors:  Keith S Barbato; Yi Luan; Daniele Ramella; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2015-11-18       Impact factor: 6.005

10.  Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct.

Authors:  Richard Y Liu; Yujing Zhou; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-02-01       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.