Asymmetric synthesis of .BETA.-amino-.ALPHA.,.ALPHA.-dimethyl-.BETA.-phenylpropionic acid. The reactions of chiral Schiff bases with dimethylketene and with reformatsky reagent.

The classical form of the Schmidt reaction involves the reaction of a carbon‐centered electrophile with hydrazoic acid with loss of nitrogen, usually with a rearrangement that forms a new carbon‐nitrogen bond. Although the conversion of a ketone into an amide is the most commonly used variation, mechanistically related versions utilize an aldehyde, acid, or a carbocation generated from an alkene or alcohol as the electrophilic component. In recent years, the definition of the Schmidt reaction has been modified to include analogous reactions in which the hydrazoic acid is replaced by an alkyl azide, promoted by Lewis acids. The use of an alkyl azide uniquely permits the formulation of intramolecular Schmidt reactions of the azide with a carbonyl or carbocationic electrophile.

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Enantiomerically Pure β‐Amino Acids from 2‐ tert ‐Butyl‐1‐Carbomethoxy‐2,3‐Dihydro‐4(1H)‐Pyrimidinone: (R)‐3‐Amino‐3‐(p‐Methoxyphenyl)Propionic Acid

Lakner

Chu

Negrete

et al. 2003

Organic Syntheses

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Enantiomerically pure β‐amino acids from 2‐ tert ‐butyl‐1‐carbomethoxy‐2,3‐dihydro‐4(1H)‐pyrimidinone: (R)‐3‐amino‐3‐(p‐methoxyphenyl)propionic acid intermediate: (S,S)‐2‐tert‐Butyl‐1‐carbomethoxy‐6‐carboxy‐2,3,5,6‐tetrahydro‐4(1H)‐pyrimidinone, 1 intermediate: (S)‐2‐tert‐Butyl‐1‐carbomethoxy‐2,3‐dihydro‐4(1H)‐pyrimidinone, 3 intermediate: 2 as a clear, colorless syrup intermediate: (R)‐2‐tert‐Butyl‐6‐(4‐methoxyphenyl)‐5,6‐dihydro‐4(1H)‐pyrimidinone product: (R)‐3‐Amino‐3‐(p‐methoxyphenyl)propionic acid intermediate: acyl aminal

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Asymmetric synthesis of .BETA.-amino-.ALPHA.,.ALPHA.-dimethyl-.BETA.-phenylpropionic acid. The reactions of chiral Schiff bases with dimethylketene and with reformatsky reagent.

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A Practical Synthesis of Enantiomerically Pure N-Benzyl-α-methyl Benzylamine

A Practical Synthesis of Enantiomerically Pure N-Benzyl-α-methyl Benzylamine

The Schmidt Reaction

Enantiomerically Pure β‐Amino Acids from 2‐ tert ‐Butyl‐1‐Carbomethoxy‐2,3‐Dihydro‐4(1H)‐Pyrimidinone: (R)‐3‐Amino‐3‐(p‐Methoxyphenyl)Propionic Acid

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