The Journal of organic chemistry

Synthesis of Orthogonally Protected (2 S)-2-Amino-adipic Acid (α-AAA) and (2 S, 4 R)-2-Amino-4-hydroxyadipic Acid (Ahad)

S Yadav, CM Taylor

Index: Yadav, Saroj; Taylor, Carol M. Journal of Organic Chemistry, 2013 , vol. 78, # 11 p. 5401 - 5409

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Citation Number: 5

Abstract

(2 S, 4 R)-2-Amino-4-hydroxyadipic acid (Ahad) building block 45 was synthesized in 11 steps and 6.5% overall yield from commercially available materials. Key steps in stereocontrol were an asymmetric conjugate addition employing a proline-based catalyst and a syn-selective intramolecular-conjugate addition of an oxygen nucleophile to an α, β- unsaturated ester. To enable incorporation of α-amino-adipic acid (α-AAA) and Ahad into ...