Enantio- and diastereoselective hetero-Diels-Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(ii) carboxamidatesThis article is part of the ChemComm 'Chirality' web themed issue.Electronic supplementary information (ESI) available. See DOI: 10.1039/c2cc32876c

The first catalytic asymmetric hetero-Diels-Alder reaction between 2-aza-3-silyloxy-1,3-butadienes and aldehydes is described. With dirhodium( ii ) tetrakis[ N -benzene-fused-phthaloyl-( S )-piperidinonate], Rh 2 ( S -BPTPI) 4 , the cycloaddition reaction proceeded exclusively in an endo mode to giv...

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Bibliographic Details
Main Authors Watanabe, Yudai, Washio, Takuya, Krishnamurthi, Janagiraman, Anada, Masahiro, Hashimoto, Shunichi
Format Journal Article
LanguageEnglish
Published 14.06.2012
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Summary:The first catalytic asymmetric hetero-Diels-Alder reaction between 2-aza-3-silyloxy-1,3-butadienes and aldehydes is described. With dirhodium( ii ) tetrakis[ N -benzene-fused-phthaloyl-( S )-piperidinonate], Rh 2 ( S -BPTPI) 4 , the cycloaddition reaction proceeded exclusively in an endo mode to give all- cis -substituted 1,3-oxazinan-4-ones in high yields with up to 98% ee. The first catalytic asymmetric hetero-Diels-Alder reaction between 2-aza-3-silyloxy-1,3-butadienes and aldehydes is described. With Rh 2 ( S -BPTPI) 4 , the cycloaddition reaction gave all- cis -substituted 1,3-oxazinan-4-ones in high yields with up to 98% ee.
Bibliography:This article is part of the
ChemComm
10.1039/c2cc32876c
Electronic supplementary information (ESI) available. See DOI
'Chirality' web themed issue.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc32876c