General and practical synthesis of (R)-phthalimido aldehydes and D-. alpha.-amino acids from D-mannitol

J Mulzer, A Angermann, B Schubert…

Index: Mulzer, Johann; Angermann, Alfred; Schubert, Boris; Seilz, Carsten Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5294 - 5299

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Citation Number: 31

Abstract

C CH2CH= CHZ d n-CSH7 e CH= CH2 a (a) See ref 7;(b)(Ph) 3P, Et02CN= NC02Et, phthalimide, THF,-10 to 22" C, 16 h;(c) MeOH, 2 N H2S04 or MeOH, CF3C-02H, 22" C, 24 h;(d) P~(OAC)~, benzene, 22" C, 15 min;(e) Jones' reagent, acetone, 0" C;(f) N2H4, EtOH, reflux. lead to optically impure products.* Our synthesis utilizes the observation7 that (R)-2, 3- isopropylideneglyceraldehyde (l), which is readily available from inexpensive D-mannitol ...