Literature DB >> 10822564

Catalytic asymmetric allylation reactions using BITIP catalysis and 2-substituted allylstannanes as surrogates for beta-keto ester dianions.

G E Keck1, T Yu.   

Abstract

[formula: see text] Catalytic asymmetric allylation (CAA) reactions using the indicated allylstannane and the BITIP catalysts previously described by us give high yields and enantioselectivities in additions to aldehydes. The products are convertible to beta-keto esters by oxidative cleavage of the olefin. These reactions thus provide a useful catalytic enantioselective method for chain extension with introduction of a versatile four-carbon unit.

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Year:  1999        PMID: 10822564     DOI: 10.1021/ol990603j

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


  4 in total

1.  A catalytic asymmetric vinylogous Mukaiyama aldol reaction.

Authors:  Lars V Heumann; Gary E Keck
Journal:  Org Lett       Date:  2007-09-21       Impact factor: 6.005

2.  Enantio- and diastereoselective additions to aldehydes using the bifunctional reagent 2-(chloromethyl)-3-(tributylstannyl)propene: application to a synthesis of the C16-C27 segment of bryostatin 1.

Authors:  Gary E Keck; Tao Yu; Mark D McLaws
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

3.  Total synthesis of (+)-dactylolide.

Authors:  Carina C Sanchez; Gary E Keck
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

4.  Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions.

Authors:  Gary E Keck; Robert L Giles; Victor J Cee; Carrie A Wager; Tao Yu; Matthew B Kraft
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

  4 in total

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