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Synthesis of Monosubstituted (S)-Oxiranes in High Optical Purity^†

Prof. Dr. Ulrich Schmidt

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)

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Dr. Jörg Talbiersky,

Dr. Jörg Talbiersky

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)

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Frank Bartkowiak,

Frank Bartkowiak

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)

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Jochen Wild,

Corresponding Author

Jochen Wild

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)Search for more papers by this author

Prof. Dr. Ulrich Schmidt,

Prof. Dr. Ulrich Schmidt

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)

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Dr. Jörg Talbiersky,

Dr. Jörg Talbiersky

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)

Search for more papers by this author

Frank Bartkowiak,

Frank Bartkowiak

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)

Search for more papers by this author

Jochen Wild,

Corresponding Author

Jochen Wild

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)

Institut für Organische Chemie, Biochemie und Isoltopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (Germany)Search for more papers by this author

First published: March 1980

https://doi.org/10.1002/anie.198001981

Citations: 23

^†

Dedicated to Professor Matthias Seefelder on the occasion of his 60th birthday

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Optically active epoxides such as (3) are useful components in the synthesis of complex chiral natural products. The simplest route to (S)-(3) probably leads from D-mannitol via diisopropylidenemannitol, (R)-(1), (S)-(2), and isomeric bromides obtained by ring opening.

References

1 E. Baer, Biochem. Prep. 2, 31 (1952).
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2Cleavage and elimination were performed under the same conditions as the reaction of glycols to give epoxides: B. T. Golding, D. R. Hall, S. Sakrikar, J. Chem. Soc. Perkin Trans. I, 1973, 1214.
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3 J. L. Coke, R. S. Shue, J. Org. Chem. 38, 2210 (1973).
10.1021/jo00952a021
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4The (S)-(5b) (α = −14°) obtained by K. Mori, Agric. Biol. Chem. 40, 1617 (1976), afforded in the completely stereoselective synthesis of (S)-massiolactone the enatiomer of the natural product in 90.5% optical purity. Assuming the reactant (S)-(5b) to have the same optical purity, then α = −15.5° can be calculated for optically pure (S)-1,2-epoxyheptane (S)-(5b); a value of α = −15.6° (c = 1.8%, ethanol) was measured.
10.1271/bbb1961.40.1617
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5Reaction conditions corresponding to G. Fouquet, M. Schlosser, Angew. Chem. 86, 50 (1974);
10.1002/ange.19740860113
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Angew. Chem. Int. Ed. Engl. 13, 82 (1974); and references cited therein.
10.1002/anie.197400821
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6 J. J. Baldwin, A. W. Raab, K. Mensler, B. H. Arison, D. E. McClure, J. Org. Chem. 43, 4876 (1978).
10.1021/jo00419a036
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7 C. R. Johnson, G. A. Dutra, J. Am. Chem. Soc. 95, 7777 (1973).
10.1021/ja00804a039
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Volume19, Issue3

March 1980

Pages 198-199

Synthesis of Monosubstituted (S)-Oxiranes in High Optical Purity^†

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Synthesis of Monosubstituted (S)-Oxiranes in High Optical Purity†

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Synthesis of Monosubstituted (S)-Oxiranes in High Optical Purity^†