Stereoselective synthesis of pinane-based β- and γ-amino acids via conjugate addition of lithium amides and nitromethane

Add time:07/30/2019    Source:sciencedirect.com

Michael addition of dibenzylamine to (−)- and (+)-tert-butyl myrtenate, (−)-2 and (+)-2, derived from (−)- and (+)-myrtenal, furnished monoterpene-based β-amino acid derivatives in highly stereospecific reactions. The resultant amino esters (−)-3 and (+)-3 were transformed to unsubstituted, mono- and disubstituted and Fmoc-protected amino acids (−)-6-11 and (+)-6-11, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles. The microwave-assisted conjugate addition of nitromethane to α,β-unsaturated esters (−)-12 and (+)-12 likewise resulted in nitro esters (−)-13 and (+)-13 in highly stereospecific reactions. Compounds (−)-13 and (+)-13 were successfully transformed into γ-amino acids (−)-16 and (+)-16 in two steps.

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