Literature DB >> 20024206

Highly enantioselective hetero-Diels-Alder reactions between Rawal's diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates.

Yudai Watanabe1, Takuya Washio, Naoyuki Shimada, Masahiro Anada, Shunichi Hashimoto.   

Abstract

The first example of a chiral Lewis acid-catalyzed enantioselective hetero-Diels-Alder (HDA) reaction between 1-dimethylamino-3-silyloxy-1,3-butadiene (Rawal's diene) and aldehydes is described. The cycloaddition reaction under the influence of 1 mol% of dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh(2)(S-BPTPI)(4), proceeded cleanly and gave, after treatment with acetyl chloride, the corresponding dihydropyranones in up to 99% ee.

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Year:  2009        PMID: 20024206     DOI: 10.1039/b919535a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  2 in total

1.  Solvent enhancement of reaction selectivity: a unique property of cationic chiral dirhodium carboxamidates.

Authors:  Xiaochen Wang; Carolin Weigl; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2011-05-27       Impact factor: 15.419

2.  Diels-Alder Reactions of 1-Alkoxy-1-amino-1,3-butadienes: Direct Synthesis of 6-Substituted and 6,6-Disubstituted 2-Cyclohexenones and 6-Substituted 5,6-Dihydropyran-2-ones.

Authors:  Pavel K Elkin; Nathaniel D Durfee; Viresh H Rawal
Journal:  Org Lett       Date:  2021-06-01       Impact factor: 6.072

  2 in total

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