Literature DB >> 15524487

Highly diastereo- and enantioselective reagents for aldehyde crotylation.

Blaine M Hackman1, Pamela J Lombardi, James L Leighton.   

Abstract

Two new, crystalline solid, storable, and highly enantioselective reagents for aldehyde crotylation have been developed. Both (cis and trans) crotylsilane reagents are easily prepared in bulk, require trivial reaction conditions, and provide the homoallylic alcohol products with near diastereo- and enantiospecificity in many cases.

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Year:  2004        PMID： 15524487     DOI： 10.1021/ol0480731

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


  28 in total

Review 1.  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

2.  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

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.  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.  Efficient asymmetric synthesis of (+)-SCH 351448.

Authors:  Sergei Bolshakov; James L Leighton
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

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.  Total synthesis of dolabelide D.

Authors:  Peter K Park; Steven J O'Malley; Darby R Schmidt; James L Leighton
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

8.  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

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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