Literature DB >> 21486033

A more comprehensive and highly practical solution to enantioselective aldehyde crotylation.

Hyunwoo Kim1, Stephen Ho, James L Leighton.   

Abstract

The enantioselective crotylation of aldehydes with 1,2-diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf)(3). The one significant limitation on the utility of these reagents--substrate scope--has thus been addressed. The net result is the most comprehensive and highly practical method for enantioselective aldehyde crotylation yet advanced.
© 2011 American Chemical Society

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Year:  2011        PMID： 21486033      PMCID： PMC3090146          DOI： 10.1021/ja200712f

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


  19 in total

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Authors:  Katsumi Kubota; James L Leighton
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-24       Impact factor: 15.336

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3.  Brønsted acid-catalyzed allylboration: short and stereodivergent synthesis of all four eupomatilone diastereomers with crystallographic assignments.

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Journal:  J Am Chem Soc       Date:  2005-09-21       Impact factor: 15.419

4.  The enantioselective allylation and crotylation of sterically hindered and functionalized aryl ketones: convenient access to unusual tertiary carbinol structures.

Authors:  Noah Z Burns; Blaine M Hackman; Pui Yee Ng; Ian A Powelson; James L Leighton
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-02       Impact factor: 15.336

5.  Catalytic enantioselective and catalyst-controlled diastereofacial-selective additions of allyl- and crotylboronates to aldehydes using chiral Brønsted acids.

Authors:  Vivek Rauniyar; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2006-04-03       Impact factor: 15.336

6.  Acceleration effect of Lewis acid in allylboration of aldehydes: catalytic, regiospecific, diastereospecific, and enantioselective synthesis of homoallyl alcohols.

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Journal:  J Am Chem Soc       Date:  2002-10-23       Impact factor: 15.419

7.  Dramatic rate enhancement with preservation of stereospecificity in the first metal-catalyzed additions of allylboronates.

Authors:  Jason W J Kennedy; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2002-10-02       Impact factor: 15.419

8.  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

9.  Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol x SnCl4 complexes. optimization, substrate scope and mechanistic investigations.

Authors:  Vivek Rauniyar; Huimin Zhai; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2008-06-07       Impact factor: 15.419

10.  Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols.

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Journal:  J Am Chem Soc       Date:  2003-08-27       Impact factor: 15.419
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  31 in total

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3.  Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation.

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5.  Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling.

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Journal:  J Am Chem Soc       Date:  2017-12-20       Impact factor: 15.419

6.  Crotylboron-based synthesis of the polypropionate units of chaxamycins A/D, salinisporamycin, and rifamycin S.

Authors:  Ming Chen; William R Roush
Journal:  J Org Chem       Date:  2012-06-15       Impact factor: 4.354

Review 7.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

8.  Diastereo- and enantioselective ruthenium-catalyzed hydrohydroxyalkylation of 2-silyl-butadienes: carbonyl syn-crotylation from the alcohol oxidation level.

Authors:  Jason R Zbieg; Joseph Moran; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-06-16       Impact factor: 15.419

9.  Harnessing the biocatalytic potential of iron- and α-ketoglutarate-dependent dioxygenases in natural product total synthesis.

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10.  Direct, Mild, and General n-Bu4NBr-Catalyzed Aldehyde Allylsilylation with Allyl Chlorides.

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