8.4.5. Nitromercuration Reactions 3878 9. Hydroamination of Alkenes and Alkynes under Microwave Irradiation 3878 * To whom correspondence should be addressed. Phone: +49 241 8

Hydroamination: direct addition of amines to alkenes and alkynes.

Cyclizations of N-acyliminium ions.

Stereocontrolled cyclofunctionalizations of double bonds through heterocyclic intermediates

5.05 – Pyridines and their Benzo Derivatives: Synthesis

The highly diastereoselective anti-aminohydroxylation of (E)-γ-tri-iso-propylsilyloxy-α,β-unsaturated esters, viaconjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine (20% yield over 7 steps), the anhydrophytosphingosine jaspine B (10% yield over 9 steps), 2-epi-jaspine B (14% yield over 9 steps), and the Prosopisalkaloid deoxoprosophylline (26% yield over 7 steps).

Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition.

L-Serine was transformed in 8 steps into (4R,5S)-2,2-dimethyl-4-[(Z)-3-pentadecenyl]-1,3-dioxan-5-amine. This chiral e,ζ-unsaturated amine was subjected to intramolecular aminomercuration and then acid hydrolysis to give (−)-deoxoprosopinine and (−)-deoxoprosophylline.

Chiral and Stereoselective Total Synthesis of (−)-Deoxoprosopinine and (−)-Deoxoprosophylline. Intramolecular Amino mercuration of an ε,ζ-Unsaturated Amine

Chiral and stereoselective total synthesis of (−)-deoxoprosopinine and (−)-deoxoprosophylline

(−)-Deoxocassine [(2R,3R,6S)-6-dodecyl-2-methyl-3-piperidinol] and its diastereomers with 2R-configuration were synthesized starting from D-alanine by a route involving the intramolecular aminomercuration of an e,ζ-unsaturated amine.

Q. Khuong-Huu

Papers

Chiral and Stereoselective Total Synthesis of (−)-Deoxoprosopinine and (−)-Deoxoprosophylline. Intramolecular Amino mercuration of an ε,ζ-Unsaturated Amine

Chiral and stereoselective total synthesis of (−)-deoxoprosopinine and (−)-deoxoprosophylline

Total Synthesis of (−)-Deoxocassine and Its Diastereomers

Chiral Acyliminium Ions in Alkaloid Synthesis: Stereospecific Formation of a (R)-12b-Indoloquinolizidinone

Piperidine alkaloids. part v. chiral and stereoselective total synthesis of (-)-deoxoprosopinine and (-)-deoxoprosophylline