910823-75-5

Upstream product

• 556-56-9 allyl iodid 
• 132047-92-8 tert-butyl(pent-4-en-1-yloxy)diphenylsilane 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 910823-73-3 (3S,4R,E)-N-allyl-4-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-1-phenylhept-1-en-3-amine 
• 910823-68-6 (3S,4R,E)-3-(allylamino)-7-(tert-butyldiphenylsilyloxy)-1-phenylhept-1-en-4-ol 
• 910823-64-2 ((E)-5-(phenylsulfonyl)pent-4-enyloxy)(tert-butyl)diphenylsilane 
• 910823-74-4 (4R,5S,E)-5-(allylamino)-4-(tert-butyldimethylsilyloxy)-7-phenylhept-6-en-1-ol 

Relevant academic research and scientific papers

Asymmetric formal synthesis of (-)-swainsonine by a highly regioselective and diastereoselective allylic amination using chlorosulfonyl isocyanate

A concise asymmetric formal synthesis of (-)-swainsonine from readily available D-erythronolactone is described. The key steps include a highly diastereoselective amination of a chiral benzylic ether, which occurs with the retention of stereochemistry using chlorosulfonyl isocyanate, and a palladium-catalyzed decarboxylative N-allylation of an allyl carbamate. Copyright

Asymmetric synthesis of anti-1,2-amino alcohols via the borono-Mannich reaction: A formal synthesis of (-)-swainsonine

Chiral α-hydroxy aldehydes generated in situ by the ADH reaction of vinyl sulfones undergo a borono-Mannich reaction with β-styrenyl boronic acid and primary amines to give anti-1,2-amino alcohols in high enantiomeric purities (83-95% ee). This new method allows much more rapid access to these valuable chiral building blocks that has been used in a short formal synthesis (10 synthetic steps from 4-penten-1-ol) of (-)-swainsonine.