Otera's catalyst
Skeletal formula of Otera's catalyst
Ball-and-stick model of the Otera's catalyst molecule
Names
Other names
Octabutyltetrathiocyanatostannoxane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/8C4H9.4CNS.2O.4Sn/c8*1-3-4-2;4*2-1-3;;;;;;/h8*1,3-4H2,2H3;;;;;;;;;;/q;;;;;;;;4*-1;;;4*+1 ☒N
    Key: BCLBTLOINGPAIT-UHFFFAOYSA-N ☒N
  • 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
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 Wada 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

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