96400-91-8

Upstream product

• 148614-15-7 (Z)-2-(chloroethyl)-2-phenyl-6-trimethylsilyl-5-hexenenitrile 
• 148614-14-6 (Z)-2-phenyl-6-trimethylsilyl-5-hexenenitrile 
• 140-29-4 phenylacetonitrile 
• 96400-88-3 4-Phenyl-4-((Z)-4-trimethylsilanyl-but-3-enyl)-3,4-dihydro-2H-pyrrole 

Downstream Products

• 35119-23-4 cis-3a-phenyl-2,3,3a,4,5,6,7,7a-octahydro-1H-indole 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF THE AMARYLLIDACEAE ALKALOID (+/-)-EPIELWESINE. THE IMPORTANCE OF VINYLSILANE STEREOCHEMISTRY IN IMINIUM ION-VINYLSILANE CYCLIZATIONS

(+/-)-Epielwesine (9) was prepared in an efficient and completely stereocontrolled fashion in six steps and 28percent overall yield from commercially available 3,4-methylenedioxyphenylacetonitrile (15a).The key step is acid promoted cyclization of the (Z)

THE IMPORTANCE OF VINYLSILANE STEREOCHEMISTRY AND ?-? STABILIZATION IN IMINIUM ION-VINYLSILANE CYCLIZATIONS. A SHORT TOTAL SYNTHESIS OF THE AMARYLLIDACEAE ALKALOID (+/-)-EPIELWESINE.

cis-3a-Aryl-2,3,3a,4,5,7a-hexahydro-1H-indoles 5 and 10 are formed in excellent yield from acid promoted cyclization of (Z)-vinylsilane imines 3 and 9.The failure of the corresponding (E)-vinylsilane isomer 4 to cyclize under similar condition demonstrate