Otera's catalyst

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Otera's catalyst
Otera's catalyst.svg
Otera's catalyst 3D ball.png
Names
Other names
Octabutyltetrathiocyanatostannoxane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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 X mark.svgN
    Key: BCLBTLOINGPAIT-UHFFFAOYSA-N X mark.svgN
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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] The reaction must be performed in nonpolar solvents in order to colocate the acid and alcohol at the catalytic center. [6]

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.
  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.
  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.
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