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

Tetrahedron

Spirobicyclic diamines. Part 3: Synthesis and metal complexation of proline-derived [4.4]-spirodiamines

F Kelleher, S Kelly, V McKee

Index: Kelleher, Fintan; Kelly, Sinead; McKee, Vickie Tetrahedron, 2007 , vol. 63, # 37 p. 9235 - 9242

Full Text: HTML

Citation Number: 11

Abstract

The syntheses of racemic and homochiral [4.4]-spirolactams, starting from l-proline, in good yields are described. Reduction of the lactam carbonyl group of spirolactams, containing chiral substituents on the lactam nitrogen, with lithium aluminium hydride, gives a series of homochiral [4.4]-spirodiamines. The crystal structure of one of these spirodiamines on complexation with zinc chloride was obtained. Interestingly it showed a hydrogen-bonded ...

1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Methyl Pyrrolidine-2-Carboxylate Structure

Methyl Pyrrolid...

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Boc-Pro-OMe Structure

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

1-tert-butyl 2-methyl 2-allylpyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Proline Structure

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Methyl Pyrrolidine-2-Carboxylate Structure

Methyl Pyrrolid...

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Boc-Pro-OMe Structure

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Proline Structure

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

1-tert-butyl 2-methyl 2-allylpyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Methyl Pyrrolidine-2-Carboxylate Structure

Methyl Pyrrolid...

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Boc-Pro-OMe Structure

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

1-tert-butyl 2-methyl 2-allylpyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Proline Structure

~%

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Methyl Pyrrolidine-2-Carboxylate Structure

Methyl Pyrrolid...

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Boc-Pro-OMe Structure

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

1-tert-butyl 2-methyl 2-allylpyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

Proline Structure

~%

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1R)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

~71%

(5S)-7-[(1R)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1R)-1-...

1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

(5S)-7-[(1R)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1R)-1-...

Proline Structure

~%

(5S)-7-[(1R)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1R)-1-...

Methyl Pyrrolidine-2-Carboxylate Structure

Methyl Pyrrolid...

~%

(5S)-7-[(1R)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1R)-1-...

Boc-Pro-OMe Structure

~%

(5S)-7-[(1R)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1R)-1-...

1-tert-butyl 2-methyl 2-allylpyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

(5S)-7-[(1R)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1R)-1-...

2-Methyl-2-propanyl (5R)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

~73%

(5R)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5R)-7-[(1S)-1-...

1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

(5R)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5R)-7-[(1S)-1-...

Methyl Pyrrolidine-2-Carboxylate Structure

Methyl Pyrrolid...

~%

(5R)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5R)-7-[(1S)-1-...

Boc-Pro-OMe Structure

~%

(5R)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5R)-7-[(1S)-1-...

1-tert-butyl 2-methyl 2-allylpyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

(5R)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5R)-7-[(1S)-1-...

Proline Structure

~%

(5R)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5R)-7-[(1S)-1-...

2-Methyl-2-propanyl (5S)-6-oxo-7-[(1S)-1-phenylethyl]-1,7-diazasp iro[4.4]nonane-1-carboxylate Structure

2-Methyl-2-prop...

~80%

(5S)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1S)-1-...

1-tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

(5S)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1S)-1-...

Methyl Pyrrolidine-2-Carboxylate Structure

Methyl Pyrrolid...

~%

(5S)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1S)-1-...

Boc-Pro-OMe Structure

~%

(5S)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1S)-1-...

Proline Structure

~%

(5S)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1S)-1-...

1-tert-butyl 2-methyl 2-allylpyrrolidine-1,2-dicarboxylate Structure

1-tert-butyl 2-...

~%

(5S)-7-[(1S)-1-Phenylethyl]-1,7-diazaspiro[4.4]nonan-6-one Structure

(5S)-7-[(1S)-1-...