Studies on the Regio- and Enantioselective Heck Arylations of Acyclic Allylic Alcohols.

Studies on the Regio- and Enantioselective Heck Arylations of Acyclic Allylic Alcohols.

Oliveira, Caio C.; Correia, Carlos Roque D.

Abstract:

Allylic alcohols is one of the most used substrates in the Heck reaction, not only because they are privileged building block in organic synthesis but also due the challenging control of the regioselectivity of the carbopalladation step. Although the styrenil adducts 3a and 4a are usually obtained as the major products, the aryl-carbonyl compounds such as 3b and 4b also represent interesting structural motifs for chemical synthesis if obtained in an enantioselective fashion (Scheme 1). Very recently, we reported the intermolecular desymmetrization of both cyclic and acyclic olefins by enantioselective Heck-Matsuda arylations (Scheme 2). As a further demonstration of the power of this method, we describe herein the more challenging arylation of non-symmetrical acyclic allylic alcohols and its applications in the synthesis of enantioenriched α- and β -aryl-aldehydes.

Allylic alcohols is one of the most used substrates in the Heck reaction, not only because they are privileged building block in organic synthesis but also due the challenging control of the regioselectivity of the carbopalladation step. Although the styrenil adducts 3a and 4a are usually obtained as the major products, the aryl-carbonyl compounds such as 3b and 4b also represent interesting structural motifs for chemical synthesis if obtained in an enantioselective fashion (Scheme 1). Very recently, we reported the intermolecular desymmetrization of both cyclic and acyclic olefins by enantioselective Heck-Matsuda arylations (Scheme 2). As a further demonstration of the power of this method, we describe herein the more challenging arylation of non-symmetrical acyclic allylic alcohols and its applications in the synthesis of enantioenriched α- and β -aryl-aldehydes.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013913141742

Referências bibliográficas

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• [6] 4 Oliveira, C. C.; Angnes, R. A.; Correia, C. R. D. J. Org. Chem. 2013, 76,
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Como citar:

Oliveira, Caio C.; Correia, Carlos Roque D.; "Studies on the Regio- and Enantioselective Heck Arylations of Acyclic Allylic Alcohols.", p-228-228. 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_2013913141742