doi: 10.1021/ol0156594.
Desymmetrization of 4-dimethylsiloxy-1,6-heptadiynes through sequential double silylformylation
Affiliations
- PMID: 11348220
- DOI: 10.1021/ol0156594
Item in Clipboard
Desymmetrization of 4-dimethylsiloxy-1,6-heptadiynes through sequential double silylformylation
Org Lett.
.
Abstract
[reaction in text] Desymmetrization of dimethylsilyloxyalkadiynes (1) by Rh-catalyzed intramolecular silylformylation affords 5-exo-(formylmethylene)oxasilacyclopentanes 2 in high yields. Novel sequential double silylformylation of 1a also provides desymmetrization, giving 3-(3-silyl-2-formylprop-2-enyl)-5-exo-(formylmethylene)oxasilacyclopentanes 4 in excellent yields. Reduction of 2a and 4 with NaBH(4) gives the corresponding 5-exo-(hydroxymethylmethylene)oxasilacyclopentanes 3a and 5, respectively.
Similar articles
-
Sterically directed iridium-catalyzed hydrosilylation of alkenes in the presence of alkynes.Org Lett. 2014 Mar 7;16(5):1330-3. doi: 10.1021/ol5000549. Epub 2014 Feb 19. Org Lett. 2014. PMID: 24552627
-
Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.Org Lett. 2008 Dec 18;10(24):5593-6. doi: 10.1021/ol802489w. Org Lett. 2008. PMID: 19007175 Free PMC article.
-
Rhodium-catalysed synthesis of multi-substituted silylindenes from aryl alkynes and hydrosilanes via C-H bond activation.Chem Commun (Camb). 2015 May 4;51(36):7685-8. doi: 10.1039/c5cc01569c. Chem Commun (Camb). 2015. PMID: 25849792
-
Vinyl-, propargyl-, and allenylsilicon reagents in asymmetric synthesis: a relatively untapped resource of environmentally benign reagents.Chemistry. 2009;15(22):5402-16. doi: 10.1002/chem.200900337. Chemistry. 2009. PMID: 19421982 Review.
-
Catalytic synthesis of oligoene and enyne derivatives through carbometalation of internal alkynes.Chem Rec. 2008;8(5):326-36. doi: 10.1002/tcr.20158. Chem Rec. 2008. PMID: 18958852 Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
