Synthesis and reactivity of β-stannylated phenylalanines
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Karin Dölling
Abstract
The free radical hydrostannation of a series of N-benzoyl and N-acetyl dehydrophenylalanine esters 2a–h yields β-stannylated phenylalanine derivatives 3 and 4. This addition of tin hydride to such unsaturated compounds simultaneously creates two new chiral centers leading to mixtures of two diastereomeric pairs of enantiomers. The reaction of 3-stannylated phenylalanine 3 with methanolic HCl yields chlorostannyl-substituted compounds 5 and 6 and, with one equivalent of bromine, the bromostannylated compounds 7 and 8 are formed. The bromostannylated phenylalanine derivative 7 reacts with one further equivalent of bromine to produce the dibromostannylated compound 9. Even the chlorostannylated phenylalanine derivative 5 reacts with one further equivalent of HCl to give the dichlorostannylated compound 10. The products were characterized by elemental analysis, infrared (IR), and multinuclear (1H, 13C, 119Sn) nuclear magnetic resonance (NMR) spectroscopy. Attempts were made to assign the preferred conformation of the stannylated phenylalanine derivatives using Karplus-type relationship of coupling constants 3J(H,H), 3J(Sn,H), and 3J(Sn,C=O). The results of these analyses have been confirmed by three crystal structure determinations.
Acknowledgments
It is a pleasure to thank Dr. André Krug (4c and 5e) and Dr. Christoph Wagner (6f) for performing the crystal structure determinations. I also wish to thank Dr. Manfred Dargatz for recording numerous NMR spectra and helpful comments.
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©2018 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- In this Issue
- Obituary
- Gérard Demazeau, 07.06.1943–03.11.2017
- Synthesis and reactivity of β-stannylated phenylalanines
- Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrile promoted by amino-functionalized CoFe2O4@SiO2 nanoparticles under conventional heating, microwave and ultrasound irradiations
- Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid. Part XII: synthesis of 5-fluoro-7-oxodihydo[1,3,4]thiadiazino [5,6-h]quinoline-8-carboxylic acid and ester
- No solid solution compounds in between the binaries: syntheses and crystal structures of Nb(Br0.62(4)Cl0.38(4))2Cl2 and NbI2Cl2
- Rare earth-rich cadmium compounds RE10TCd3 (RE=Y, Tb, Dy, Ho, Er, Tm, Lu; T=Rh, Pd, Ir, Pt) with an ordered Co2Al5-type structure
- Aminkomplexe des Goldes, Teil 9: Gold(I)-halogenid-Komplexe mit primären und azyklischen sekundären Aminen und ihre Oxidation zu Gold(III)-Derivaten
- Erratum
- Berichtigung: Phosphanchalkogenide und ihre Metallkomplexe. II. Komplexe einiger Gold(I)-Halogenide mit Diphosphanmonochalkogeniden
Articles in the same Issue
- Frontmatter
- In this Issue
- Obituary
- Gérard Demazeau, 07.06.1943–03.11.2017
- Synthesis and reactivity of β-stannylated phenylalanines
- Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrile promoted by amino-functionalized CoFe2O4@SiO2 nanoparticles under conventional heating, microwave and ultrasound irradiations
- Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid. Part XII: synthesis of 5-fluoro-7-oxodihydo[1,3,4]thiadiazino [5,6-h]quinoline-8-carboxylic acid and ester
- No solid solution compounds in between the binaries: syntheses and crystal structures of Nb(Br0.62(4)Cl0.38(4))2Cl2 and NbI2Cl2
- Rare earth-rich cadmium compounds RE10TCd3 (RE=Y, Tb, Dy, Ho, Er, Tm, Lu; T=Rh, Pd, Ir, Pt) with an ordered Co2Al5-type structure
- Aminkomplexe des Goldes, Teil 9: Gold(I)-halogenid-Komplexe mit primären und azyklischen sekundären Aminen und ihre Oxidation zu Gold(III)-Derivaten
- Erratum
- Berichtigung: Phosphanchalkogenide und ihre Metallkomplexe. II. Komplexe einiger Gold(I)-Halogenide mit Diphosphanmonochalkogeniden
