R-(–)-Pantolactole in the Julia-Kocienski Reaction

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Abstract

It was demonstrated that in the KHMDS-promoted reaction of (3R)-3-(1-ethoxyethoxy)-4,4- dimethyltetrahydrofuran-2-olwith 5-(methylsulfonyl)-1-phenyl-1H-tetrazole, an anomalous heteroaryl acetal of pantolactone is formed: 5-{[(2S,3R)-3-(1-ethoxyethoxy)-4,4-dimethyltetrahydrofuran-2-yl] oxy}-1-phenyl-1H-tetrazole.

About the authors

G. R. Sunagatullina

Ufa Institute of Chemistry - a separate structural unit of the Federal State Budgetary Scientific Institution Ufa Federal Research Centre of the Russian Academy of Sciences

Email: gsunagatullina95@mail.ru
ORCID iD: 0000-0002-2691-1801
prosp. Oktyabrya 71, Ufa, 450054 Russia

N. K. Seleznyova

Ufa Institute of Chemistry - a separate structural unit of the Federal State Budgetary Scientific Institution Ufa Federal Research Centre of the Russian Academy of Sciences

Email: gsunagatullina95@mail.ru
ORCID iD: 0000-0002-9917-1912
prosp. Oktyabrya 71, Ufa, 450054 Russia

A. N. Lobov

Ufa Institute of Chemistry - a separate structural unit of the Federal State Budgetary Scientific Institution Ufa Federal Research Centre of the Russian Academy of Sciences

Email: gsunagatullina95@mail.ru
ORCID iD: 0000-0002-9223-508X
prosp. Oktyabrya 71, Ufa, 450054 Russia

M. S. Miftakhov

Ufa Institute of Chemistry - a separate structural unit of the Federal State Budgetary Scientific Institution Ufa Federal Research Centre of the Russian Academy of Sciences

Email: gsunagatullina95@mail.ru
ORCID iD: 0000-0005-2836-4249
prosp. Oktyabrya 71, Ufa, 450054 Russia

References

  1. Kocienski P.J. Phosphorous and Sulfur and Relat. Elements. 1985, 24, 97–127. http://doi.org/10.1080/03086648508073398
  2. Blakemorea P.R., Colea W.J., Kocienski P.J., Morley A. Synlett. 1998, 1, 26–28. http://doi.org/10.1055/s-1998-1570
  3. Kocienski P.J., Bell A., Blakemore P.R. Synlett. 2000, 3, 365–366. http://doi.org/10.1055/s-2000-6536
  4. Julia M., Paris J.-M. Tetrahedron Letters. 1973, 14 (49), 4833–4836. http://doi.org/10.1016/s00 40-4039(01)87348-2
  5. Truce W.E., Kreider E.M., Brand W.W. Organic Reactions. 1970, 18, 99–215. http://doi.org/10.1002/0 471264180.or018.02
  6. Ma J.-H., Wang F., Wang J.-X., You Q.-D. Chinese J. Org. Chem. 2010, 30 (11), 1615–1623.
  7. Chatterjee B., Bera S., Mondal D. Tetrahedron: Asymmetry. 2014, 25, 1–55. http://doi.org/10.1016/j.tetasy.2013.09.027
  8. Aïssa C. Eur. J. Org. Chem. 2009, 12, 1831–1844. http://doi.org/10.1002/ejoc.200801117
  9. Blakemore P. R. J. Chem. Soc., Perkin Trans. 2002, 1 (23), 2563–2585. http://doi.org/10.1039/B208078H
  10. Коротченко В.Н., Ненайденко В.Г., Баленкова Е.С., Шастин а.В. Успехи химии. 2004, 73 (10), 1039–1074.
  11. Colombo M.I., Zinczuk J., Mischne M.P., Rùveda E.A. Tetrahedron: Asymmetry. 2001, 12 (9), 1251–1253. http://doi.org/10.1016/s0957-4166(01)00222-1 http://doi.org/10.1016/s0957-4166(01)00222-1
  12. Corbet M., Bourdon B., Gueyrard D., Goekjian P.G. Tetrahedron Letters. 2008, 49 (5), 750–754. http://doi.org/10.1016/j.tetlet.2007.11.207
  13. Smith G.M.T., Burton P.M., Bray C.D. Synthetic Methods. 2015, 127, 15451–15455. http://doi.org/10.1002/ange.201508467
  14. Валеев Р.Ф., Сунагатуллина Г.Р., Лоза В.В., Лобов а.Н., Мифтахов М.С. ЖОрХ. 2021, 57, 802–819. [Valeev R.F., Sunagatullina G.R., Loza V.V., Lobov A.N., Miftakhov M.S. Russ. J. Org. Chem. 2021, 57, 889–904. http://doi.org/10.1134/S1070428021060038]
  15. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Carica- 1 to M., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnenberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgome- 1 ry J.A., Peralta J. E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Rega N., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Dapprich S., Daniels A.D., Farkas O., Foresman J.B., Ortiz J.V., Cioslowski J., Fox D.J. Gaussian 09, Revision C.01. Gaussian, Inc., Wallingford CT, 2010.
  16. Jain R., Bally T., Rablen P.R. J. Org. Chem. 2009, 74 (11), 4017–4023. http://doi.org/10.1021/jo900482q
  17. Bally T., Rablen P.R. J. Org. Chem. 2011, 76 (12), 4818– 4830. http://doi.org/10.1021/jo200513q

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