Organocatalytic Michael reaction study between phenyl acetaldehyde and nitrostyrene

Organocatalytic Michael reaction study between phenyl acetaldehyde and nitrostyrene

Gandolfi Donadío, Lucía; Galetti, Mariana A.; Giorgi, Gianluca; Comin, Maria J.

Abstract:

Organocatalytic Michael addittion has been intensively studied in recent years and provides Michael adducts in a highly stereoselective way. We were interested in developing a simple and stereocontrolled route to 3,4-diphenyl substituted pyrrolidines, that are structural motifs found in many biologically active compounds, using a Michael reaction between nitrostyrenes and benzylic aldehydes as the key step. Extensive studies on the organocatalyzed Michael reaction between nitroalkenes and aliphatic aldehydes were conducted showing a high syn diastereselection according to Seebach’s model. However, only four examples using α-unsubstituted benzylic aldehydes have been reported and they showed a relative low syn diasteroselectivity. Since the higher acidity of the α protons of benzylic aldehydes relative to aliphatic ones could affect the reaction mechanism, we decided to examine and optimize the diastereochemical outcome of this process. Herein we report our results concerning diastereoselective Michael reaction between phenylacetaldehyde and nitrostyrene.

Organocatalytic Michael addittion has been intensively studied in recent years and provides Michael adducts in a highly stereoselective way. We were interested in developing a simple and stereocontrolled route to 3,4-diphenyl substituted pyrrolidines, that are structural motifs found in many biologically active compounds, using a Michael reaction between nitrostyrenes and benzylic aldehydes as the key step. Extensive studies on the organocatalyzed Michael reaction between nitroalkenes and aliphatic aldehydes were conducted showing a high syn diastereselection according to Seebach’s model. However, only four examples using α-unsubstituted benzylic aldehydes have been reported and they showed a relative low syn diasteroselectivity. Since the higher acidity of the α protons of benzylic aldehydes relative to aliphatic ones could affect the reaction mechanism, we decided to examine and optimize the diastereochemical outcome of this process. Herein we report our results concerning diastereoselective Michael reaction between phenylacetaldehyde and nitrostyrene.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013823112450

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Como citar:

Gandolfi Donadío, Lucía; Galetti, Mariana A.; Giorgi, Gianluca; Comin, Maria J.; "Organocatalytic Michael reaction study between phenyl acetaldehyde and nitrostyrene", p-202-202. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013823112450