Literature DB >> 12095334

Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes.

James W A Kinnaird1, Pui Yee Ng, Katsumi Kubota, Xiaolun Wang, James L Leighton.   

Abstract

A new reagent for the enantioselective allylation of aliphatic aldehydes has been developed. The reagent is easily prepared in a single step from commercially available materials and may be stored without significant decomposition. The reactivity of the reagent is attributed to strain-release Lewis acidity.

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Year:  2002        PMID： 12095334     DOI： 10.1021/ja0264908

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


  33 in total

1.  Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors:  Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal:  Aldrichimica Acta       Date:  2008       Impact factor: 3.667

Review 2.  Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

Authors:  John F Bower; In Su Kim; Ryan L Patman; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Polyketide assembly by alkene-alkyne reductive cross-coupling: spiroketals through the union of homoallylic alcohols.

Authors:  Daniel P Canterbury; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

4.  Vinylogous aldol products from chiral crotylsilanes obtained by enantioselective Rh(II) and Cu(I) carbenoid Si-H insertion.

Authors:  Jie Wu; Yu Chen; James S Panek
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

5.  Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids.

Authors:  Marc Liniger; Yiyang Liu; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2017-09-25       Impact factor: 15.419

6.  SYNTHESIS OF (S,S)-DIISOPROPYL TARTRATE (E)-CROTYLBORONATE AND ITS REACTION WITH ALDEHYDES: (2R,3R,4R)-1,2-DIDEOXY-2-ETHENYL-4,5-O-(1-METHYLETHYLIDENE)-XYLITOL.

Authors:  Huikai Sun; William R Roush; David A Candito; Mathieu Blanchot; Mark Lautens
Journal:  Organic Synth       Date:  2011

7.  Iridium-catalyzed allylation of chiral β-stereogenic alcohols: bypassing discrete formation of epimerizable aldehydes.

Authors:  Daniel C Schmitt; Anne-Marie R Dechert-Schmitt; Michael J Krische
Journal:  Org Lett       Date:  2012-12-11       Impact factor: 6.005

8.  Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination.

Authors:  Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

9.  SYNTHESIS OF (+)-B-ALLYLDIISOPINOCAMPHEYLBORANE AND ITS REACTION WITH ALDEHYDES.

Authors:  Huikai Sun; William R Roush; David Hughes
Journal:  Organic Synth       Date:  2011

10.  Improved method for the synthesis of beta-carbonyl silyl-1,3-dithianes by the double conjugate addition of 1,3-dithiol to propargylic carbonyl compounds.

Authors:  Sumit Mukherjee; Dimitra Kontokosta; Aditi Patil; Sivakumar Rallapalli; Daesung Lee
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354
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