Synthesis 2020; 52(08): 1211-1214
DOI: 10.1055/s-0039-1690830
psp
© Georg Thieme Verlag Stuttgart · New York

Practical Preparation of Cyclopropenone 1,3-Propanediol Ketal

,
Robin Heckershoff
,
Marc Zimmer
,
Further Information

Publication History

Received: 01 January 2020

Accepted after revision: 28 January 2020

Publication Date:
24 February 2020 (online)


Abstract

Cyclopropenone 1,3-propanediol ketal is an increasingly versatile building block for the introduction of various C3 and dioxaspiro units due to the emergence of numerous methodologies for the application of strained hydrocarbons. This Practical Synthetic Procedure gives an updated synthesis for a basic ketal of cyclopropenone with lowered solvent toxicity and a detailed step-by-step guide for the safe production of potassium amide in liquid ammonia and for its application in the synthesis of the cyclopropene ring.

Supporting Information

Primary Data

 
  • References

  • 1 New address: F. F. Mulks, Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern, Switzerland.
    • 2a Breslow R, Pecoraro J, Sugimoto T. Org. Synth. 1977; 57: 41
    • 2b Boger LD, Brotherton CE, Georg GI. Org. Synth. 1987; 65: 32
    • 3a Isaka M, Ejiri S, Nakamura E. Tetrahedron 1992; 48: 2045
    • 3b Isaka M, Ando R, Nakamura E. Tetrahedron Lett. 1991; 32: 1339
  • 4 Szmant HH. Organic Building Blocks of the Chemical Industry. Wiley; New York: 1989
  • 5 Seidel G, Mynott R, Fürstner A. Angew. Chem. Int. Ed. 2009; 48: 2510 ; Angew. Chem. 2009, 121, 2548
  • 6 Mulks FF, Antoni PW, Rominger F, Hashmi AS. K. Adv. Synth. Catal. 2018; 360: 1810
  • 7 Mulks FF, Antoni PW, Gross JH, Graf J, Rominger F, Hashmi AS. K. J. Am. Chem. Soc. 2019; 141: 4687
  • 8 Trofimov A, Rubina M, Rubin M, Gevorgyan V. J. Org. Chem. 2007; 72: 8910
    • 9a Boger DL, Brotherthon CE. Tetrahedron 1986; 42: 2777
    • 9b Patel PR, Boger DL. Org. Lett. 2010; 12: 3540
    • 9c Levandowski BJ, Houk KN. J. Am. Chem. Soc. 2016; 138: 16731
    • 10a Walsh R. Chem. Soc. Rev. 2005; 34: 714
    • 10b Zhu Z.-B, Wei Y, Shi M. Chem. Soc. Rev. 2011; 40: 5534
    • 10c Vicente R. Synthesis 2016; 48: 2343