Otera's catalyst

Otera's catalyst
Names
	Other names Octabutyltetrathiocyanatostannoxane
Identifiers
CAS Number	95971-03-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	17621074 ;
PubChem CID	16689150;
	InChI InChI=1S/8C4H9.4CNS.2O.4Sn/c81-3-4-2;42-1-3;;;;;;/h81,3-4H2,2H3;;;;;;;;;;/q;;;;;;;;4-1;;;4*+1 Key: BCLBTLOINGPAIT-UHFFFAOYSA-N ;
	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). verify (what is ?) 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 Wada and coworkers, and elaborated upon by Otera and coworkers.

Preparation

This class of compounds may be prepared generally by the reaction of an organotin halide and oxide:

2 R₂SnO + 2 R₂SnX₂ → (XR₂SnOSnR₂X)₂

In particular, the thiocyanate compound was prepared by the reaction of dibutyltin oxide with dibutyltin diisothiocyanate. Otherwise, this compound is not commercially available.

Applications

This thiocyanate compound can be used as a transesterification catalyst. Although it is not well known, it has been used in a number of total syntheses.

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. The reaction must be performed in nonpolar solvents in order to colocate the acid and alcohol at the catalytic center.

References

1 2 Wada, M.; Nishino, M.; Okawara, R. (1965). "Preparation and properties of dialkyltin isothiocyanate derivatives". J. Organomet. Chem. 3: 70–75. doi:10.1016/S0022-328X(00)82737-0.
1 2 3 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.
1 2 Otera, Junzo. (1993). "Transesterification". Chem. Rev. 93 (4): 1449–1470. 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.
↑ Stiles, Dylan (3 May 2006). "falling in love with otera's catalyst". Tenderblog. Archived from the original on 27 July 2006. Retrieved 4 January 2025.

[wada-1] 1 2 Wada, M.; Nishino, M.; Okawara, R. (1965). "Preparation and properties of dialkyltin isothiocyanate derivatives". J. Organomet. Chem. 3: 70–75. doi:10.1016/S0022-328X(00)82737-0.

[otera-2] 1 2 3 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] 1 2 Otera, Junzo. (1993). "Transesterification". Chem. Rev. 93 (4): 1449–1470. 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.

[6] Stiles, Dylan (3 May 2006). "falling in love with otera's catalyst". Tenderblog. Archived from the original on 27 July 2006. Retrieved 4 January 2025.