158499-74-2

Upstream product

• 599-04-2 (R)-Pantolacton 
• 277317-84-7 (2R/S,3R)-3-(Benzyloxy)tetrahydro-4,4-dimethylfuran-2-ol 
• 20374-33-8 (R)-(+)-3-(Benzyloxy)-4,5-dihydro-4,4-dimethyl-furan-2(3H)-on 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 158499-73-1 (R)-(+)-3-(Benzyloxy)-3-(1,3-dithian-2-yl)-2,2-dimethylpropan-1-ol 

Downstream Products

• 158499-75-3 (5R,2E)-(+)-5-(Benzyloxy)-5-(1,3-dithian-2-yl)-4,4-dimethylpent-2-ensaeure-ethylester 
• 158499-76-4 (5R,2E)-5-(Benzyloxy)-4,4-dimethyl-6-oxohex-2-ensaeure-ethylester 
• 158499-77-5 (1S,3R,4R)-(-)-<3-(Benzyloxy)-4-hydroxy-2,2-dimethylcyclobutyl>essigsaeure-ethylester 
• 241473-87-0 2-(E,2R)-2-(Benzyloxy)-3,3-dimethyl-5-(phenylsulfonyl)pent-4-enal 
• 158499-79-7 (1S,3R)-<3-(Benzyloxy)-2,2-dimethyl-4-oxocyclobutyl>essigsaeure-ethylester 
• 158499-78-6 (1S,3S)-<3-(Benzyloxy)-2,2-dimethylcyclobutyl>essigsaeure-ethylester 
• 277317-89-2 2-[(E,1R)-1-(benzyloxy)-2,2-dimethyl-4-(phenylsulfonyl)but-3-enyl]-1,3-dithiane 

Relevant academic research and scientific papers

Samarium(ii)-mediated 4-exo-trig cyclisations of unsaturated aldehydes. a stereoselective approach to functionalised cyclobutanols

γ,δ-Unsaturated aldehydes having a fully substituted centre in either the α- or β-positions, have been prepared from substituted γ-butyrolactones and undergo efficient 4-exo-trig cyclisation on treatment with sarnarium(ii) iodide to give functionalised cyclobutanols. In all cases cyclisation occurs with complete diastereocontrol to give anti-cydobutanol products. The stereochemistry of the products has been confirmed by NOE and X-ray crystallographic studies. In the cyclisation of substrates having a third substituent on the double bond, α- to the ester, significant control is achieved at the third newly formed stereocentre lying outside the ring. The origin of the stereoselectivity at this third centre and its marked dependence on cosolvent are discussed. The Royal Society of Chemistry 2000.

Radical-Type Cyclization of Dienes, IX. - On the Stereoselectivity of the Radical 4-exo-trig-Cyclization of Optically Active Ethyl (2E)-6-Oxohex-2-enoates with Samarium(II) Iodide

Ethyl (5R,2E)-5-(benzyloxy)-4,4-dimethyl-6-oxohex-2-enoate (9) was prepared from (R)-(-)-pantolactone (3) by a series of straightforward reactions.The reaction of 9 with samarium(II) iodide produces enantiomerically pure ethyl (1S,3R,4R)-(-)-3-(benzyloxy