(2S, 3R)-2-acetooxymethanyl-3-(P-nitrophenyl)-N-tosylaziridine 5 was synthesized from (1S, 2S)-2-amino-1-(4-nitrophenyl)-1, 3-propanediol 1 in four steps with a 24.8% overall yield. This reaction is stereospecific and...(2S, 3R)-2-acetooxymethanyl-3-(P-nitrophenyl)-N-tosylaziridine 5 was synthesized from (1S, 2S)-2-amino-1-(4-nitrophenyl)-1, 3-propanediol 1 in four steps with a 24.8% overall yield. This reaction is stereospecific and occurs an expectable configuration inversion at α-carbon atom of benzyl group. The structure of substituted aziridine was determined on FT-IR, NMR, MS and so on.展开更多
Started from 5-hydroxy-2-pentanone, (R)(E)-3,7-dimethyl-2-octene-1,8-dioic acid, callosobruchusic acid, was synthesized via five steps with D-(-)-camphor sultam as the chiral auxiliary. It was of good optical purity a...Started from 5-hydroxy-2-pentanone, (R)(E)-3,7-dimethyl-2-octene-1,8-dioic acid, callosobruchusic acid, was synthesized via five steps with D-(-)-camphor sultam as the chiral auxiliary. It was of good optical purity and yield.展开更多
(+) Camphor derived N crotonoylsultam 2, readily available from chiral auxiliary bornane 10,2 sultam and crotonoyl chloride, reacted with selected Grignard reagent 3(R= n butyl, n pentyl , n ...(+) Camphor derived N crotonoylsultam 2, readily available from chiral auxiliary bornane 10,2 sultam and crotonoyl chloride, reacted with selected Grignard reagent 3(R= n butyl, n pentyl , n hexyl, n heptyl) under the control of CuI or not being at low temperatures, giving diasteroisomers 4, 5 respectively. After nondestructive cleavage both enantiomers of the acid and alcohol were obtained in high e.e .%. The d.e .% of 4,5 was determined by HPLC, and the assignment of these values was discussed by analyzing 1H NMR(500 MHz).展开更多
( 3R,4S )-4-Methyl-3-hexanol and ( 3R,4S )-4-methyl-3-heptanol, which are the pheromones of ant Tetramorium impurm and Leptogenys diminuta , were stereoselectively synthesized by six step sequence starting from N born...( 3R,4S )-4-Methyl-3-hexanol and ( 3R,4S )-4-methyl-3-heptanol, which are the pheromones of ant Tetramorium impurm and Leptogenys diminuta , were stereoselectively synthesized by six step sequence starting from N bornane 10,2 sultam separately, the two asymmetric carbon atoms of the target products were created by employing asymmetric syn aldolization of N acylbornane 10,2 sultam with propylaldehyde. The enantiomeric excess of the target products prepared by this route is over 92%.展开更多
potential chiral auxilliary, (+)-camphor derived N-propionyl sultam, wassynthesized from (+ )-camphor-10-sulphonyl chloride in four steps with enan-tiomerical purity. The molecular and crystal structures of the title ...potential chiral auxilliary, (+)-camphor derived N-propionyl sultam, wassynthesized from (+ )-camphor-10-sulphonyl chloride in four steps with enan-tiomerical purity. The molecular and crystal structures of the title compound weredetermined by single crystal diffraction analysis. The crystal belongts to monoclin-ic , space group P2_1 with cell dimentions a= 1. 0502(4) , b= 0. 7252(1 ) , c= 0. 9363(2) nm, β= 108. 3(5) , V = 0. 677 nm￣3, F(000) = 292 and Z= 2. The structuralcharacteristics with respect to the potential utility for the stereoselective alkylationat a-carbon of the N-propionyl group are discussed and explained based on ￣1H-, ￣(13)C-NMR. MS and X-ray analysis.展开更多
基金Supported by the science and technology fund of Wuhan city (No:996 0 0 10 16 G)
文摘(2S, 3R)-2-acetooxymethanyl-3-(P-nitrophenyl)-N-tosylaziridine 5 was synthesized from (1S, 2S)-2-amino-1-(4-nitrophenyl)-1, 3-propanediol 1 in four steps with a 24.8% overall yield. This reaction is stereospecific and occurs an expectable configuration inversion at α-carbon atom of benzyl group. The structure of substituted aziridine was determined on FT-IR, NMR, MS and so on.
基金Supported by the National Natural Science Foundation of China( No. 2 9872 0 12)
文摘Started from 5-hydroxy-2-pentanone, (R)(E)-3,7-dimethyl-2-octene-1,8-dioic acid, callosobruchusic acid, was synthesized via five steps with D-(-)-camphor sultam as the chiral auxiliary. It was of good optical purity and yield.
文摘(+) Camphor derived N crotonoylsultam 2, readily available from chiral auxiliary bornane 10,2 sultam and crotonoyl chloride, reacted with selected Grignard reagent 3(R= n butyl, n pentyl , n hexyl, n heptyl) under the control of CuI or not being at low temperatures, giving diasteroisomers 4, 5 respectively. After nondestructive cleavage both enantiomers of the acid and alcohol were obtained in high e.e .%. The d.e .% of 4,5 was determined by HPLC, and the assignment of these values was discussed by analyzing 1H NMR(500 MHz).
文摘( 3R,4S )-4-Methyl-3-hexanol and ( 3R,4S )-4-methyl-3-heptanol, which are the pheromones of ant Tetramorium impurm and Leptogenys diminuta , were stereoselectively synthesized by six step sequence starting from N bornane 10,2 sultam separately, the two asymmetric carbon atoms of the target products were created by employing asymmetric syn aldolization of N acylbornane 10,2 sultam with propylaldehyde. The enantiomeric excess of the target products prepared by this route is over 92%.
文摘potential chiral auxilliary, (+)-camphor derived N-propionyl sultam, wassynthesized from (+ )-camphor-10-sulphonyl chloride in four steps with enan-tiomerical purity. The molecular and crystal structures of the title compound weredetermined by single crystal diffraction analysis. The crystal belongts to monoclin-ic , space group P2_1 with cell dimentions a= 1. 0502(4) , b= 0. 7252(1 ) , c= 0. 9363(2) nm, β= 108. 3(5) , V = 0. 677 nm￣3, F(000) = 292 and Z= 2. The structuralcharacteristics with respect to the potential utility for the stereoselective alkylationat a-carbon of the N-propionyl group are discussed and explained based on ￣1H-, ￣(13)C-NMR. MS and X-ray analysis.
