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,^[1] and elaborated upon by Otera and coworkers.^[2]

Preparation edit

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 edit

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 edit

^ ^a ^b 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ ^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 (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.

[wada-1] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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 (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.

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