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

Autor:	Bahamonde A; Department of Chemistry , University of Utah , 315 S. 1400 E , Salt Lake City , Utah 84112 , United States., Al Rifaie B; Department of Chemistry , University of Utah , 315 S. 1400 E , Salt Lake City , Utah 84112 , United States., Martín-Heras V; Department of Chemistry , University of Utah , 315 S. 1400 E , Salt Lake City , Utah 84112 , United States., Allen JR; Department of Chemistry , University of Utah , 315 S. 1400 E , Salt Lake City , Utah 84112 , United States., Sigman MS; Department of Chemistry , University of Utah , 315 S. 1400 E , Salt Lake City , Utah 84112 , United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2019 Jun 05; Vol. 141 (22), pp. 8708-8711. Date of Electronic Publication: 2019 May 24.
DOI:	10.1021/jacs.9b03438
Abstrakt:	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 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 α-tertiary amines.
Databáze:	MEDLINE
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