- Otera's catalyst
-
Otera's catalyst 
Identifiers ChemSpider 21106460 
Jmol-3D images Image 1 - CCCC[Sn]1([N](=C=S)[Sn]2(O1[Sn]3(O2[Sn]([N]3=C=S)(CCCC)(CCCC)C=C=S)(CCCC)CCCC)(CCCC)CCCC)(CCCC)C=C=S
- InChI=1S/8C4H9.2C2HS.2CNS.2O.4Sn/c8*1-3-4-2;2*1-2-3;2*2-1-3;;;;;;/h8*1,3-4H2,2H3;2*1H;;;;;;;;
Key: OUBFKIZYHPMZHQ-UHFFFAOYSA-N
InChI=1/8C4H9.2C2HS.2CNS.2O.4Sn/c8*1-3-4-2;2*1-2-3;2*2-1-3;;;;;;/h8*1,3-4H2,2H3;2*1H;;;;;;;;/rC38H74N2O2S4Sn4/c1-9-17-27-47(35-25-43,28-18-10-2)39(37-45)49(31-21-13-5,32-22-14-6)41(47)50(33-23-15-7,34-24-16-8)40(38-46)48(36-26-44,42(49)50,29-19-11-3)30-20-12-4/h35-36H,9-24,27-34H2,1-8H3
Key: OUBFKIZYHPMZHQ-BIWIHVFOAY
Properties Molecular formula C36H72N4O2S4Sn4 Molar mass 1196.08 g mol−1 
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references Otera's catalyst is an organostannane compound which has been used as a transesterification catalyst. This isothioscyanate compound is a member of a family of organostannanes reported by Wasada and coworkers,[1] and elaborated upon by Otera and coworkers.[2]
Preparation
This class of compounds may be prepared generally by the reaction of an organotin halide and oxide:[3]
- 2 R2SnO + 2 R2SnX2 → (XR2SnOSnR2X)2
In particular, the thiocyanate compound was prepared by the reaction of dibutyltin oxide with dibutyltin diisothiocyanate.[1] Otherwise, this compound is not commercially available.
Applications
This thiocyanate compound can be used as a transesterification catalyst.[2] Although it is not well known, it has been used in a number of total syntheses.[4][5]
In this application, the reaction occurs via the displacement of the bridging isothiocyanate ligands with the incoming alcohol to form an alcohol-bridged active catalyst. Tin acts as the Lewis acid, and gives the transesterified product.[2][3]
References
- ^ a b Wada, M (1965). "Preparation and properties of dialkyltin isothiocyanate derivatives". J. Organomet. Chem. 3: 70. doi:10.1016/S0022-328X(00)82737-0.
- ^ a b c Otera, J et al (1991). "Novel template effects of distannoxane catalysts in highly efficient transesterification and esterification". J. Org. Chem. 56 (18): 5307–5311. doi:10.1021/jo00018a019.
- ^ a b Otera, Junzo. (1993). "Transesterification". Chem. Rev. 93: 1449. doi:10.1021/cr00020a004.
- ^ Trost, BM et al (2005). "Synthesis of Amphidinolide P". J. Am. Chem. Soc. 127 (50): 17921–17937. doi:10.1055/s-2006-941939. PMC 2533515. PMID 16351124. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2533515.
- ^ Trost, BM; Stiles, DT (2007). "Total Synthesis of Spirotryprostatin B via Diastereoselective Prenylation". Org. Lett. 9 (15): 2763. doi:10.1021/ol070971k. PMID 17592853.
Categories:- Organotin compounds
- Catalysts
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