e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

A New General Approach to Enantiomerically Pure Cyclic and Open??Chain (R)??and (S)?螃?, α??Disubstituted α??Amino Acids

…, P Schönholzer, K Müller, H Heimgartner…

Index: Obrecht; Spiegler; Schonholzer; Muller; Heimgartner; Stierli Helvetica Chimica Acta, 1992 , vol. 75, # 5 p. 1666 - 1696

Full Text: HTML

Citation Number: 89

Abstract

Abstract A wide range of cyclic and open-chain α, α-disubstituted α-amino acids 1a-p were prepared. The racemic N-acylated α, α-disubstituted amino acids were resolved by coupling to chiral amines 15-18 derived from (S)-phenylalanine to form diastereoisomers 19/20 or 21/22 that could be separated by crystallization and/or flash chromatography on silica gel (Scheme 3). Selective cleavage via the 1, 3-oxazol-5 (4H)-ones 10a-p gave the ...

Pyrrolidine Structure

Boc-L-phenylalanine Structure

Boc-L-phenylalanine

~%

H-PHE-PYRROLIDIDE Structure

H-PHE-PYRROLIDIDE

5-(4'-METHOXYBENZYL)-5-METHYLHYDANTOIN Structure

5-(4'-METHOXYBE...

~93%

O-a-Dimethyl Tyrosine Structure

O-a-Dimethyl Ty...

4-Methoxyphenylacetone Structure

4-Methoxyphenyl...

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

~94%

5-(4'-METHOXYBENZYL)-5-METHYLHYDANTOIN Structure

5-(4'-METHOXYBE...

3',4'-dihydro-5'-methoxyspiro[imidazolidine-4,2'(1'H)-naphthalene]-2,5-dione Structure

3',4'-dihydro-5...

~87%

2-amino-5-methoxy-3,4-dihydro-1H-naphthalene-2-carboxylic acid Structure

2-amino-5-metho...

5-Methoxy-2-tetralone Structure

5-Methoxy-2-tet...

~%

2-amino-5-methoxy-3,4-dihydro-1H-naphthalene-2-carboxylic acid Structure

2-amino-5-metho...

1-Cyclopropylethanone Structure

1-Cyclopropylet...

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

~79%

5-cyclopropyl-5-methyl-imidazolidine-2,4-dione Structure

5-cyclopropyl-5...

N2-((S)-N2-acetylvalyl)-L-phenylalanine dimethylamide Structure

N2-((S)-N2-acet...

~91%

Acetylvaline Structure

3',4'-dihydro-8'-methoxyspiro[imidazolidine-4,2'(1'H)-naphthalene]2,5-dione Structure

3',4'-dihydro-8...

~82%

2-NAPHTHALENECARBOXYLIC ACID, 2-AMINO-1,2,3,4-TETRAHYDRO-8-METHOXY- Structure

2-NAPHTHALENECA...

8-Methoxy-2-tetralone Structure

8-Methoxy-2-tet...

~%

2-NAPHTHALENECARBOXYLIC ACID, 2-AMINO-1,2,3,4-TETRAHYDRO-8-METHOXY- Structure

2-NAPHTHALENECA...

3-phenyl-2-[(2-phenylacetyl)amino]propanoic acid Structure

3-phenyl-2-[(2-...

~%

N-(Phenylacetyl)-L-phenylalanine Structure

N-(Phenylacetyl...

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

b-Tetralone Structure

~90%

Tetrantoin Structure

N2-[(S)-N2-(phenylacetyl)phenylalanyl]-L-phenylalanine dimethylamide Structure

N2-[(S)-N2-(phe...

~76%

N-(Phenylacetyl)-L-phenylalanine Structure

N-(Phenylacetyl...

2,4-dibenzyl-4H-oxazol-5-one Structure

2,4-dibenzyl-4H...

~%

N-(Phenylacetyl)-L-phenylalanine Structure

N-(Phenylacetyl...

5-cyclopropyl-5-methyl-imidazolidine-2,4-dione Structure

5-cyclopropyl-5...

~97%

2-AMINO-2-CYCLOPROPYLPROPIONIC ACID Structure

2-AMINO-2-CYCLO...

1-Cyclopropylethanone Structure

1-Cyclopropylet...

~%

2-AMINO-2-CYCLOPROPYLPROPIONIC ACID Structure

2-AMINO-2-CYCLO...

6-Methoxy-3,4-dihydronaphthalen-2(1H)-on Structure

6-Methoxy-3,4-d...

~%

2-AMINO-6-METHOXY-1,2,3,4-TETRAHYDRO-NAPHTHALENE-2-CARBOXYLIC ACID Structure

2-AMINO-6-METHO...

6,7-Dimethoxy-2-tetralone Structure

6,7-Dimethoxy-2...

POTASSIUM CYANIDE Structure

POTASSIUM CYANIDE

~84%

2-spirohydantoin-6,7-dimethoxytetrahydronaphthalene Structure

2-spirohydantoi...

7-Methoxyspiro[tetralin-2,4'-imidazolidine]-2',5'-dione Structure

7-Methoxyspiro[...

~91%

2-amino-7-methoxy-3,4-dihydro-1H-naphthalene-2-carboxylic acid Structure

2-amino-7-metho...

7-Methoxy-3,4-dihydronaphthalen-2(1H)-one Structure

7-Methoxy-3,4-d...

~%

2-amino-7-methoxy-3,4-dihydro-1H-naphthalene-2-carboxylic acid Structure

2-amino-7-metho...