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Synthesis 2011(12): 1859-1864
DOI: 10.1055/s-0030-1260460
DOI: 10.1055/s-0030-1260460
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkFormation of Functionalized Cyclopentenes via Catalytic Asymmetric [3+2] Cycloaddition of Acrylamides with an Allenoate Promoted by Dipeptide-Derived Phosphines
Weitere Informationen
Received
18 March 2011
Publikationsdatum:
05. Mai 2011 (online)
Publikationsverlauf
Publikationsdatum:
05. Mai 2011 (online)

Abstract
Acrylamides derived from 3,5-dimethyl-1H-pyrazole are employed in the asymmetric [3+2] cycloaddition with the allenoate, tert-butyl buta-2,3-dienoate, for the first time. d-Threonine-l-tert-leucine-based bifucntional phosphines are effective catalysts for the above reactions, affording regiospecific [3+2]-annulation products in excellent yields and with moderate enantioselectivities.
Key words
[3+2] cycloaddition - chiral phosphines - amino acids - bifunctional phosphine catalysts
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