Literature DB >> 12926924

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

Hugo Lachance1, Xiaosong Lu, Michel Gravel, Dennis G Hall.   

Abstract

A general approach for the allylation of aldehydes using stable, air-tolerant camphor-based chiral allylboronates under Sc(OTf)3 catalysis is described. This practical methodology provides both syn and anti propionate units and other homoallylic alcohols with very high levels of diastereo- and enantioselectivity for several substrates, including functionalized aliphatic aldehydes useful toward the elaboration of complex natural products.

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Year:  2003        PMID： 12926924     DOI： 10.1021/ja036807j

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


  16 in total

1.  Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

2.  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

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

Authors:  Hyunwoo Kim; Stephen Ho; James L Leighton
Journal:  J Am Chem Soc       Date:  2011-04-12       Impact factor: 15.419

4.  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

5.  Catalytic enantioselective 1,2-diboration of 1,3-dienes: versatile reagents for stereoselective allylation.

Authors:  Laura T Kliman; Scott N Mlynarski; Grace E Ferris; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-01       Impact factor: 15.336

6.  Establishing the absolute configuration of the asbestinins: enantioselective total synthesis of 11-acetoxy-4-deoxyasbestinin D.

Authors:  Michael T Crimmins; J Michael Ellis
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

7.  Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability.

Authors:  Abbas Hassan; Ian A Townsend; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2011-08-10       Impact factor: 6.222

8.  Enantioselective homocrotylboration of aliphatic aldehydes.

Authors:  Hongkun Lin; Wenbo Pei; Hao Wang; Kendall N Houk; Isaac J Krauss
Journal:  J Am Chem Soc       Date:  2012-12-26       Impact factor: 15.419

9.  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

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

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