Otera's catalyst

Otera's catalyst
Names
	Other names Octabutyltetrathiocyanatostannoxane
Identifiers
CAS Number	95971-03-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	21106460 ;
	InChI InChI=1S/8C4H9.2C2HS.2CNS.2O.4Sn/c81-3-4-2;21-2-3;22-1-3;;;;;;/h81,3-4H2,2H3;21H;;;;;;;; Key: OUBFKIZYHPMZHQ-UHFFFAOYSA-N ; InChI=1/8C4H9.2C2HS.2CNS.2O.4Sn/c81-3-4-2;21-2-3;22-1-3;;;;;;/h81,3-4H2,2H3;21H;;;;;;;;/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;
	SMILES CCCC[Sn]1(N(=C=S)[Sn]2(O1[Sn]3(O2[Sn](N3=C=S)(CCCC)(CCCC)N=C=S)(CCCC)CCCC)(CCCC)CCCC)(CCCC)N=C=S;
Properties
Chemical formula	C36H72N4O2S4Sn4
Molar mass	1196.08 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Otera's catalyst, named after Japanese chemist Junzo Otera, 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]

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References

Wada, M (1965). "Preparation and properties of dialkyltin isothiocyanate derivatives". J. Organomet. Chem. 3: 70. doi:10.1016/S0022-328X(00)82737-0.
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.
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:10.1021/ja055967n. PMC 2533515. PMID 16351124.
Trost, BM; Stiles, DT (2007). "Total Synthesis of Spirotryprostatin B via Diastereoselective Prenylation". Org. Lett. 9 (15): 2763–6. doi:10.1021/ol070971k. PMID 17592853.

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[wasada-1] Wada, M (1965). "Preparation and properties of dialkyltin isothiocyanate derivatives". J. Organomet. Chem. 3: 70. doi:10.1016/S0022-328X(00)82737-0.

[otera-2] 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.

[otera-chemrev-3] Otera, Junzo. (1993). "Transesterification". Chem. Rev. 93: 1449. doi:10.1021/cr00020a004.

[4] Trost, BM; et al. (2005). "Synthesis of Amphidinolide P". J. Am. Chem. Soc. 127 (50): 17921–17937. doi:10.1021/ja055967n. PMC 2533515. PMID 16351124.

[5] Trost, BM; Stiles, DT (2007). "Total Synthesis of Spirotryprostatin B via Diastereoselective Prenylation". Org. Lett. 9 (15): 2763–6. doi:10.1021/ol070971k. PMID 17592853.