Enantioselective Diels–Alder Reaction Induced by Chiral Supramolecular Lewis Acid Catalysts Based on CN···B and PO···B Coordination Bonds.

Autor:	Hatano, Manabu, Hayashi, Kazushi, Sakamoto, Tatsuhiro, Makino, Yuma, Ishihara, Kazuaki
Předmět:	MOLECULAR structure of boranes COORDINATE covalent bond SUPRAMOLECULAR chemistry CHEMICAL inhibitors LEWIS acids DIOLEFINS ALDEHYDE derivatives
Zdroj:	Synlett; 2016, Vol. 27 Issue 7, p1061-1067, 7p
Abstrakt:	Chiral supramolecular boron Lewis acid catalysts were prepared from chiral 3-phosphoryl-1,1'-bi-2-naphthols, (2-cyanophenyl) boronic acids, and tris(pentafluorophenyl)borane, bound through CN•••B and PO•••B coordination bonds. In particular, the coordinated tris(pentafluorophenyl)boranes increase the Lewis acidity of the active center in the manner of a Lewis acid assisted Lewis acid catalyst system. A possible cavity in these catalysts was highly suitable for several Diels–Alder probe reactions of acroleins with cyclic or acyclic dienes, which gave the corresponding adducts in good to high yields and high enantioselectivities. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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