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2005
Enantioselective syntheses
O 0031
Oxadiazinones as Chiral Auxiliaries: Increased Diastereoselectivities in the GlyAldol Reaction of Oxadiazinones. — The use of an N4-isopropyloxadiazinone
12- 037 colate
residue as chiral template allows for highly diastereoselective glycolate aldol reaction
of amide (I) with aldehydes (II). Selectivities of up to 98% d.e. are achieved. The oxadiazinone auxiliary is readily cleaved off in alkaline solution, and the target dihydroxypropionate (V) is formed in 95% optical purity after a few protection—deprotection
steps. — (VAUGHN, J. F.; HITCHCOCK*, S. R.; Tetrahedron: Asymmetry 15 (2004)
21, 3449-3455; Dep. Chem., Ill. State Univ., Normal, IL 61790, USA; Eng.) —
Mischke
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