New 1,3-amino alcohols derived from enantiopure bridgehead β-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acids

Abstract

Constrained enantiopure bicyclic β-amino acids derived from the asymmetric Diels-Alder reaction of the (R)-benzyl-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)-benzoate and the 1-(benzyloxycarbonylamino)cyclohexadiene provide original templates for the construction of new rigid enantiopure 1,3-amino alcohols.

Synthesis of Enantiopure 1,2-Diaminobicyclo[2.2.2]octane Derivatives, C1-Symmetric Chiral 1,2-Diamines with a Rigid Bicyclic Backbone

“…The combined organic phases were dried over Na 2 SO 4 , filtered, and concentrated under reduced pressure, affording the expected compound 7 (1.96 g, 95%). HPLC, MS (ESI) analysis, and NMR spectroscopic data were consistent with those previously described for the ( R ) enantiomer …”

“…HPLC, MS (ESI) analysis, and NMR spectroscopic data were consistent with those previously described for the (R) enantiomer. 24 Experimental Procedure for Curtius Rearrangement. Experimental Procedure for the Synthesis of "mix"-6 and "mix"-8 (example).…”

Syntheses of Four Enantiomers of 2,3-Diendo- and 3-Endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic Acid and Their Saturated Analogues

“…While a range of stereoselective syntheses of enantiomerically enriched small (three- or four-membered: [11,12,13] and medium (five- to eight-membered) cyclic [14,15,16,17] and sterically hindered bicyclic norbornane and norbornene β-amino acids [18,19] or their derivatives have been reported, relatively few examples cocerning the synthesis and applications of enantiomerically enriched bicyclo[2.2.2]octane β-amino acid derivatives have been described [20,21,22,23,24].…”