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Enantioselective Markovnikov Addition of Carbamates to Allylic Alcohols for the Construction of ?-Secondary and ?-Tertiary Amines.

ABSTRACT: Herein we describe the development of a Pd-catalyzed enantioselective Markovnikov addition of carbamates to allylic alcohols for the construction of ?-tertiary and ?-secondary amines. The reaction affords a range of ?-amino alcohols, after reduction of the aldehyde in situ, which contain a variety of functional groups in moderate yields and moderate to good enantioselectivities. These products can be readily oxidized to ?-amino acids, valuable building blocks for the synthesis of biologically active compounds. Mechanistic studies indicate that the C-N bond formation occurs via a syn amino-palladation mechanism, an insight which may guide future reaction development given the limited number of enantioselective syntheses of ?-tertiary amines.

SUBMITTER: Bahamonde A 

PROVIDER: S-EPMC6583784 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Enantioselective Markovnikov Addition of Carbamates to Allylic Alcohols for the Construction of α-Secondary and α-Tertiary Amines.

Bahamonde Ana A   Al Rifaie Buthainah B   Martín-Heras Victor V   Allen Jamie R JR   Sigman Matthew S MS  

Journal of the American Chemical Society 20190524 22

Herein we describe the development of a Pd-catalyzed enantioselective Markovnikov addition of carbamates to allylic alcohols for the construction of α-tertiary and α-secondary amines. The reaction affords a range of β-amino alcohols, after reduction of the aldehyde in situ, which contain a variety of functional groups in moderate yields and moderate to good enantioselectivities. These products can be readily oxidized to β-amino acids, valuable building blocks for the synthesis of biologically ac  ...[more]

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