Synthesis and Applications of Cyclopropanones and Their Equivalents as Three-Carbon Building Blocks in Organic Synthesis

Yujin Jang; Roger Machín-Rivera; Vincent N. G. Lindsay

doi:10.1055/a-1519-1670

Synthesis, Table of Contents

Synthesis 2021; 53(21): 3909-3934
DOI: 10.1055/a-1519-1670

review

Synthesis and Applications of Cyclopropanones and Their Equivalents as Three-Carbon Building Blocks in Organic Synthesis

Yujin Jang‡

,

Roger Machín-Rivera ‡

,

Vincent N. G. Lindsay ∗

Abstract

All articles of this category

Dedicated to the memory of Prof. Harry H. Wasserman

Abstract

Cyclopropanone derivatives constitute highly strained cycloalkanones with promising applications as three-carbon building blocks in organic synthesis. Due to the presence of a ketone in such a small ring system, all C–C bonds and the carbonyl group are considered to be labile in suitable conditions, leading to a wide variety of synthetic disconnections, including nucleophilic addition, ring expansion, ring-opening, and (formal) cycloaddition. Despite their synthetic potential, the widespread adoption of cyclopropanones as substrates has been considerably hampered by the difficulties associated with the preparation and storage of such unstable compounds, prompting the development of cyclopropanone surrogates that can equilibrate to the parent ketone in situ via elimination. This review summarizes the syntheses and applications of cyclopropanone derivatives and their equivalents, and offers a perspective of the state of the field as well as its expected future directions.

1 Introduction

2 Preparation of Cyclopropanones and Their Equivalents

2.1 Carbenoid Chemistry

2.2 Allene Oxide Rearrangement

2.3 Ring Closure by Dehydrohalogenation or Dehalogenation

2.4 Photolytic Processes

2.5 Miscellaneous Formation of Cyclopropanones

2.6 Cyclopropanone Equivalents

3 Synthetic Applications of Cyclopropanones and Their Equivalents

3.1 Nucleophilic Addition to the Carbonyl Group

3.2 Ring Expansion

3.3 Ring-Opening

3.4 Cycloaddition and Formal Cycloaddition

4 Conclusion and Outlook

Key words

cyclopropanone - ring strain - oxyallyl - Favorskii - homoenolate - ring expansion - ring opening

Full Text

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73a Erden I, Amputch MA. Tetrahedron Lett. 1987; 28: 3779
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For recent reviews on the metal homoenolate chemistry and other ring-opening reactions of cyclopropanols and cyclopropanone (hemi)ketals, see:

74a McDonald TR, Mills LR, West MS, Rousseaux SA. L. Chem. Rev. 2021; 121: 3
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74c Nikolaev A, Orellana A. Synthesis 2016; 48: 1741
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75d Schaafsma SE, Jorritsma R, Steinberg H, de Boer ThJ. Tetrahedron Lett. 1973; 14: 827

76a Bakker BH, Schilder GJ. A, Bok TR, Steinberg H, de Boer ThJ. Tetrahedron 1973; 29: 93
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For a related study on the use of organic oxidants in the radical ring-opening of cyclopropanone ketals, see:

76c Abe M, Oku A. Tetrahedron Lett. 1994; 35: 3551

77a Abe M, Oku A. J. Chem. Soc., Chem. Commun. 1994; 1673
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For another example of β-radical trapping with alkenes following oxidative ring-opening, see:

77c Iwasawa N, Hayakawa S, Funahashi M, Isobe K, Narasaka K. Bull. Chem. Soc. Jpn. 1993; 66: 819

78 Wu L, Wang L, Chen P, Guo Y, Liu G. Adv. Synth. Catal. 2020; 362: 2189

79a Nakamura E, Kuwajima I. J. Am. Chem. Soc. 1977; 99: 7360
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For related seminal studies performed on cyclopropanols, see:

79m Nickon A, Lambert JL, Oliver JE, Covey DF, Morgan J. J. Am. Chem. Soc. 1976; 98: 2593

80a Nakamura E, Kuwajima I. J. Am. Chem. Soc. 1984; 106: 3368
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81 Aoki S, Fujimura T, Nakamura E, Kuwajima I. J. Am. Chem. Soc. 1988; 110: 3296

82a Turro NJ, Edelson SS, Williams JR, Thomas RD. J. Am. Chem. Soc. 1968; 90: 1926
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83a Noordstrand AA. P, Steinberg H, de Boer ThJ. Tetrahedron Lett. 1975; 16: 2611
83b Wiering PG, Steinberg H. J. Org. Chem. 1981; 46: 1663

84a Wiering PG, Verhoeven JW, Steinberg H. J. Am. Chem. Soc. 1981; 103: 7675
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85a Crimmins MT, Nantermet PG. J. Org. Chem. 1990; 55: 4235
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86a Skorianetz W, Schulte-Elte KH, Ohloff G. Helv. Chim. Acta 1971; 54: 1913
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87 Erden I, Xu F.-P, Drummond J, Alstad R. J. Org. Chem. 1993; 58: 3611
88 Jang Y, Lindsay VN. G. Org. Lett. 2020; 22: 8872

89a Khand IU, Knox GR, Pauson PL, Watts WE, Foreman MI. J. Chem. Soc., Perkin Trans. 1 1973; 975

For reviews on the Pauson–Khand reaction, see:

89b Brummond KM, Kent JL. Tetrahedron 2000; 56: 3263
89c Blanco-Urgoiti J, Anorbe L, Perez-Serrano L, Dominguez G, Perez-Castells J. Chem. Soc. Rev. 2004; 33: 32
89d Kurteva VB, Afonso CA. M. Chem. Rev. 2009; 109: 6809

For an analogous mechanism employing cyclobutanones instead of cyclopropanone, see:

90a Murakami M, Ashida S, Matsuda T. J. Am. Chem. Soc. 2005; 127: 6932
90b Murakami M, Ashida S, Matsuda T. J. Am. Chem. Soc. 2006; 128: 2166
90c Murakami M, Itahashi T, Ito Y. J. Am. Chem. Soc. 2002; 124: 13976
90d Murakami M, Ashida S. Chem. Commun. 2006; 4599
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91a Kascheres A, Correa Filho J, Cunha S. Tetrahedron 1993; 49: 381

For related transformations of cyclopropenones, see:

91b Kascheres A, Kascheres C, Rodrigues JA. R, Santana AR. A. J. Org. Chem. 1976; 41: 3546
91c Eicher T, Angerer EV, Hansen A.-M. Liebigs Ann. Chem. 1971; 746: 102

92a Cho SY, Lee HI, Cha JK. Org. Lett. 2001; 3: 2891

For other selected examples of (4+3) cycloadditions involving oxyallyl intermediates, see:

92b Noyori R, Baba Y, Makino S, Takaya H. Tetrahedron Lett. 1973; 14: 1741
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92d Vinter JG, Hoffmann HM. R. J. Am. Chem. Soc. 1973; 95: 3051
92e Schmid R, Schmid H. Helv. Chim. Acta 1974; 57: 1883
92f Föhlisch B, Gehrlach E, Herter R. Angew. Chem., Int. Ed. Engl. 1982; 21: 137
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