Highly Enantioselective Michael Addition of Nitroalkanes to Chalcones Using Chiral Squaramides as Hydrogen Bonding Organocatalysts

A series of squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low catalyst loading under high temperature (80 °C),...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 23; pp. 5450 - 5453
Main Authors Yang, Wen, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.12.2010
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
THIOLS
ASYMMETRIC CONJUGATE ADDITION
ALPHA,BETA-UNSATURATED KETONES
ENONES
CATALYST
DERIVATIVES
NITROMETHANE
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Summary:A series of squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low catalyst loading under high temperature (80 °C), affording the desired R or S enantiomers of the products flexibly in high yields with excellent enantioselectivities (93−96% ee) by the appropriate choice of organocatalysts.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol102294g