ChemInform Abstract: Combined α,α‐Dialkylprolinol Ether/Broensted Acid Promotes Mannich Reactions of Aldehydes with Unactivated Imines. An Entry to anti‐Configured Propargylic Amino Alcohols.

Abstract

Combined α,α-Dialkylprolinol Ether/Broensted Acid Promotes Mannich Reactions of Aldehydes with Unactivated Imines. An Entry to anti-Configured Propargylic Amino Alcohols. -A series of amino alcohols (III) and (IX) is prepared with 80-98% diastereomeric excess using a hitherto not reported enamine-mediated antiselective Mannich reaction of corresponding imines with aldehydes (II). -(GOMEZ-BENGOA, E.; JIMENEZ, J.; LAPUERTA, I.; MIELGO, A.; OIARBIDE, M.; OTAZO, I.; VELILLA, I.; VERA, S.; PALOMO*, C.; Chem. Sci. 3 (2012) 10, 2949-2957, http://dx.doi.org/10.1039/c2sc20590d ; Dep. Quim. Org., Fac. Quim., Univ. Pais Vasco, E-20080 San Sebastian, Spain; Eng.) -R. Staver 12-058