Synthesis of Diastereoisomeric 4-Dimethylamino-3-phenyl-2-butanols and Related Esters for Antimicrobial Evaluation

The isomerization of N,O-acetals 1 yields N-acyl-0-vinyl amino)aldehydes 3. The relative configurations of the proacetals 2 or 2-aminomethyl-l,3-butadienes 10, depending on ducts 3 have been determined by X-ray analysis and 'Hthe nature of the nitrogen substituents. In the presence of NMR experiments. The mechanism of the reaction is discustrimethylsilyl trifluoromethanesulfonate (TMSOTf) the N,O-sed. Crossover experiments indicate an intermolecular acetals 2h-u are converted stereoselectively into P-(N-acyl-course of the rearrangement. In connection with our investigations of the stereoselective rearrangements of alkyl vinyl a c e t a l~ [~~] to aldol ethers, we have also studied the reactions of 0-vinyl N,O-acetals. In this paper we report on the diastereoselective synthesis of p-(N-acy1amino)aldehydes 3 in three simple steps from easily accessible starting materials via N,O-acetals 1 and 2 (Scheme l)[331. The type of catalyst depends on the nitrogen substituents of the starting materials (Table 2).

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Synthesis and Evaluation of 1 - (Hydroxyphenyl) -1 -nonen-3-ones and Related Compounds for Antineoplastic and Antimicrobial Activities

Dimmock

Nyathi

Smith

1978

Journal of Pharmaceutical Sciences

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Synthesis of Diastereoisomeric 4-Dimethylamino-3-phenyl-2-butanols and Related Esters for Antimicrobial Evaluation

Cited by 6 publications

References 13 publications

ChemInform Abstract: SYNTHESIS OF DIASTEREOISOMERIC 4‐DIMETHYLAMINO‐3‐PHENYL‐2‐BUTANOLS AND RELATED ESTERS FOR ANTIMICROBIAL EVALUATION

ChemInform Abstract: SYNTHESIS OF DIASTEREOISOMERIC 4‐DIMETHYLAMINO‐3‐PHENYL‐2‐BUTANOLS AND RELATED ESTERS FOR ANTIMICROBIAL EVALUATION

Stereoselective Amidoalkylation Reactions via N,O‐Acetals

Synthesis and Evaluation of 1 - (Hydroxyphenyl) -1 -nonen-3-ones and Related Compounds for Antineoplastic and Antimicrobial Activities

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