419541-63-2

Upstream product

• 60656-87-3 benzyloxyacetoaldehyde 
• 112897-03-7 3-(tert-butyldiphenylsilyloxy)-1-propanal 
• 164662-96-8 1-trimethylsilyl-2-(tributylstannyl)methyl-2-propene 
• 419541-71-2 (3S)-1-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-5-(2,2-dimethyl-2-silapropil)hex-5-en-3-ol 
• 129601-00-9 3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propionitrile 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 419541-42-7 (2R)-4-(2,2-dimethyl-2-silapropyl)-1-(phenylmethoxy)pent-4-en-2-ol 

Downstream Products

• 419541-48-3 2-{(6R,2S)-4-methylene-6-[(phenylmethoxy)methyl]-3,5,6-trihydro-2H-pyran-2-yl}ethanal 
• 940877-37-2 [(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-iodomethyl-but-3-enyl ester 
• 940877-36-1 [(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid (S)-1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3-chloromethyl-but-3-enyl ester 
• 940877-34-9 [(2S,6R)-6-benzyloxymethyl-4-methylene-tetrahydropyran-2-yl]-acetic acid 
• 419541-69-8 2-{(6R,2S)-4-methylene-6-[(phenylmethoxy)methyl]-3,5,6-trihydro-2H-pyran-2-yl}ethan-1-ol 

Relevant academic research and scientific papers

Enantioselective Synthesis of cis-2,6-Disubstituted-4-methylene Tetrahydropyrans via Chromium Catalysis?

Enantioenriched 2,6-disubstituted 4-methylene tetrahydropyrans have been obtained via a two-step sequence consisting of a highly enantioselective chromium-catalyzed carbonyl 2-(trimethylsilyl methyl)allylation and Prins cyclization. Commercially available (2-(chloromethyl)allyl)trimethylsilane serves as the bifunctional linchpin to combine two aldehydes to assemble the 2,6-disubstituted pyrans. A variety of functional groups are compatible under the mild reaction conditions. The synthetic utility of this methodology was demonstrated by the asymmetric synthesis of 16 examples of homoallylic alcohol and 8 examples of 2,6-disubstituted 4-methylene tetrahydropyrans, including an advanced intermediate which could be transformed to natural product centrolobine via a known procedure.

Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

[reaction: see text] A reaction process for the asymmetric construction of a variety of cis or trans disubstituted pyrans is described. This sequences allows for the asymmetric convergent union of two aldehydes with silyl-stannane reagent 1 in a two-step