Tetrahedron

A practical large scale chemical synthesis of chiral glycines

K Ramalingam, P Nanjappan, DM Kalvin, RW Woodard

Index: Ramalingam, Kondareddiar; Nanjappan, Palaniappagownder; Kalvin, Douglas M.; Woodard, Ronald W. Tetrahedron, 1988 , vol. 44, # 17 p. 5597 - 5604

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Citation Number: 20

Abstract

(R)-and (S)-[2-2H] glycine of high chiral purity were synthesized in large quantities in≈ 40% overall yield from readily available starting materials via a totally chemical procedure. Reduction of either [1-2H]-furfural or [1-2H]-4-methoxybenzaldehyde with either (+) or (-)-B- isopinocampheyl-9-borabicyclo [3.3. 1] nonane gave chiral arylmethyl alcohols which were converted into their respective phthaloyl amino derivatives of the opposite configuration at ...