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Asymmetric synthesis of (R)-2-[3-(methoxymethoxy)propyl]- 3,3-diphenyl-1-tosyl-1,3-azasilinan-6-one

Azasilanes have excellent bioactivities; however, asymmetric synthesis of azasilinan-6-one with a substitution at the second potion has been investigated very little. In this paper, (R)-2-[3-(methoxymethoxy)propyl] -3,3-diphenyl-1-tosyl-1,3-azasilinan-6-one was successfully synthesized. | JOURNAL OF SCIENCE OF HNUE Chemical and Biological Sci. 2014 Vol. 59 No. 9 pp. 3-10 This paper is available online at http stdb.hnue.edu.vn ASYMMETRIC SYNTHESIS OF R -2- 3- METHOXYMETHOXY PROPYL - 3 3-DIPHENYL-1-TOSYL-1 3-AZASILINAN-6-ONE Duong Quoc Hoan1 and Scott McN. Sieburth2 1 Faculty of Chemistry Hanoi National University of Education 2 Department of Chemistry Temple University the United States of America Abstract. Azasilanes have excellent bioactivities however asymmetric synthesis of azasilinan-6-one with a substitution at the second potion has been investigated very little. In this paper R -2- 3- methoxymethoxy propyl -3 3-diphenyl-1-tosyl-1 3-azasilinan-6-one was successfully synthesized. The chiral center of silylsulfinamide was prepared by the addition of silyl lithium to R -Davis chiral sulfinimine. Cyclization of δ-amino carboxylic acid gave 1 3-azasilinan-6-one that can be an important product to synthesize 2-substituted 1 3-azasilinan rings. Structures of all new compounds were confirmed by IR 1 H and 13 C-NMR along with the exact mass. Keywords Synthesis R -2- 3- methoxymethoxy propyl -3 3-diphenyl-1-tosyl-1 3- -azasilinan-6-one IR 1 H and 13 C-NMR. 1. Introduction Nitrogen-containing heterocycles constitute structural frameworks in a plethora of pharmaceuticals and alkaloids and are essential components of the pharmacophore 2 3 6 . In recent years there has been an interest in the preparation of heterocycles in which one of the ring carbons has been replaced by silicon atoms. A few bioactive silicon-nitrogen heterocycles have thus far been synthesized and screened for bioactivity. For example the dopamine receptor antagonist silahaloperidol 1 Figure 1 displays improved selectivity compared to haloperidol. Furthermore its metabolic fate in human liver microsomas does not produce a silicon analogue of the neurotoxic metabolite HPP Hereditary pyropoikilocytosis which is responsible for the severe side effects of haloperidol 4 . Other heterocyclic .