The Crabbé homologation of terminal alkynes could be applied to the synthesis of 1,3-disubstituted allenes using aldehydes, N,N-dicyclohexylamine, and a catalytic amount of copper(I) iodide. The key to this success was the employment of an excess of aldehyde and amine, and performing the reaction under microwave irradiation conditions.
Planar Chiral [2.2]Paracyclophane-Based Phosphine-Broensted Acid Catalysts Bearing Exceptionally High Reactivity for Aza-Morita-Baylis-Hillman Reaction. -New title compounds are synthesized and tested as catalysts. Best results are obtained with PCP which affords the products with good e.e's. -(KITAGAKI*, S.; OHTA, Y.; TAKAHASHI, R.; KOMIZU, M.; MUKAI, C.; Tetrahedron Lett. 54 (2013) 5, 384-386, http://dx.
Can the Crabbé Homologation Be Successfully Applied to the Synthesis of 1,3-Disubstituted Allenes? -The one-pot process under optimized conditions can be successfully applied to the preparation of title compounds (III) from alkynes and aldehydes in the presence of amine. They are also obtained from propargylamines under similar conditions. -(KITAGAKI*, S.; KOMIZU, M.; MUKAI, C.; Synlett 2011, 8, 1129-1132, http://dx.doi.org/10.1055/s-0030-1259936 ; Div. Pharm. Sci., Grad. Sch. Nat. Sci. Technol., Kanazawa Univ., Kanazawa 920-11, Japan; Eng.) -Mais 37-052
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