A new route to the synthesis of amino acids through the mercury cyclization of chiral amidals

…, G Cardillo, C Tomasini, P Tortoreto

Index: Amoroso, Rosa; Cardillo, Giuliana; Tomasini, Claudia; Tortoreto, Paola Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1082 - 1087

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Citation Number: 30

Abstract

By means of the mercury cyclization of the unsaturated amidals 3a-0, obtained from the reaction of 1, 3, 5-tris-[(S)-phenylethyl] hexahydrotriazine (1) and a,@-unsaturated acyl chlorides, diastereomeric mixtures of im-idazolidin-4ones 5-8 and perihydropyrimidin-4- ones 4-10 have been synthesized and easily separated by flash, chromatography. The subsequent hydrolysis under acid conditions of the separated heterocycles affords ...

 Related Synthetic Route
(1'S,5R)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-5-butylimidazolidin-4-one Structure

138261-25-3

(1'S,5R)-1-(ben...

~81%

H-D-Nle-OH Structure

327-56-0

H-D-Nle-OH

(1'S,6S)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-6-phenylperihydropyrimidin-4-one Structure

138261-26-4

(1'S,6S)-1-(ben...

~69%

3 Amino-phenylpropionic acid Structure

3646-50-2

3 Amino-phenylp...

1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-6,6-dimethylperihydropyrimidin-4-one Structure

138261-28-6

1-(benzyloxycar...

~74%

3-Amino-3-methylbutanoic acid Structure

625-05-8

3-Amino-3-methy...

(1'S,5R)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-5-(hydroxymethyl)imidazolidin-4-one Structure

138261-21-9

(1'S,5R)-1-(ben...

~66%

D-serine Structure

312-84-5

D-serine

N/A Structure

138261-23-1

N/A

~68%

H-D-Abu-OH Structure

2623-91-8

H-D-Abu-OH

N/A Structure

131969-00-1

N/A

~72%

D-alanine Structure

338-69-2

D-alanine


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