148583-99-7

Upstream product

• 75-24-1 trimethylaluminum 
• 88158-68-3 4-(tert-butyldiphenylsilyloxy)-1-butyne 
• 78592-73-1 (E)-4-iodo-3-methylbut-3-en-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 498556-45-9 (E)-tert-butyl-(3-methyl-6-(trimethylsilanyl)hex-3-en-5-ynyloxy)diphenylsilane 
• 864914-93-2 (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-4-methyl-hex-3-enal 
• 864915-12-8 (E)-(2R,3S)-7-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-5-methyl-hept-4-ene-1,2-diol 
• 864915-16-2 (1R,4S,5S)-4-[(E)-(1S,2S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-4-methyl-hex-3-enyl]-7,7-dimethyl-2-oxa-bicyclo[3.2.0]heptan-3-one 
• 498556-46-0 (E)-tert-butyl-(3-methylhex-3-en-5-ynyloxy)diphenylsilane 
• 1332864-71-7 C₃₅H₃₈Cl₄N₂O₅Si 
• 1332864-58-0 (E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol 
• 1332865-02-7 (E)-(tert-butyl) 2-((5-(tert-butyl)diphenylsilyloxy)-3-methylpent-1-en-3-yl)diazenecarboxylate 
• 1332864-72-8 (E)-(tert-butyl) 1-(5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-enyl)hydrazinecarboxylate 
• 1332864-57-9 (E)-ethyl 5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-enoate 
• 148615-77-4 (11S,12S,13R)-15-(tert-butyldiphenylsilyloxy)-12,13-epoxy-ent-labd-7-en-11-ol 

Relevant academic research and scientific papers

Diastereoselective Additions of Chiral Vinylzinc Reagents to α-Chiral Aldehydes

(Matrix presented) Additions of vinylic zinc bromide reagents to α-chiral aldehydes (R1 = CH2OTBS, R2 = Me; R1 = Me, R2 = OTBS) in the presence of lithiated (+)- or (-)-N-methylephedrine proceed with

Dimethylzinc-mediated additions of alkenylzirconocenes to aldimines. New methodologies for allylic amine and C-cyclopropylalkylamine syntheses

Hydrozirconation of alkynes with zirconocene hydrochloride followed by in situ transmetalation to dimethylzinc provides access to reactive alkenyl organometallic reagents from readily available precursors. Upon addition of imines, 1,2-attack leads to synthetically useful allylic amine building blocks. In the presence of CH2I2 or CH2Cl2, the N-metalated allylic amide intermediate is cyclopropanated and C-cyclopropylalkylamines are formed in high yield and excellent diastereoselectivities favoring the anti products. The use of enynes as starting materials for this domino reaction provides conjugated biscyclopropanes and thus allows the stereoselective formation of five new carbon-carbon bonds. A transition state that explains the need for both zirconocene complex and alkyl zinc in the cyclopropanation reaction is proposed.

SYNTHESIS OF AN ADVANCED FORSKOLIN INTERMEDIATE

The 8,13-epoxylabdane derivative rac-19 was prepared in eight steps commencing from (E,E)-farnesol (8).Key reactions are the formation of 7 from drimenal (9b) and 6, Sharpless I epoxidation (7->11), epoxy alcohol oxidation (11->16), reductive epoxide cleavage (16->15), peracid epoxidation (15->18), and the trimethylsilyl triflate-mediated conversion of 18 into 19.