Bifunctionalized Allenes. Part XXIII. An Efficient Method for Regioselective Synthesis of 5-Phosphorylated Allenecarboxylates-Reference-Cited by-同舟云学术

Bifunctionalized Allenes. Part XXIII. An Efficient Method for Regioselective Synthesis of 5-Phosphorylated Allenecarboxylates

Published:2020-11-01 Issue:3 Volume:7 Page:1-10
ISSN:2367-5144
Container-title:Acta Scientifica Naturalis
language:en
Short-container-title:

Author:

Hasanov Hasan H.¹,Ivanov Ivaylo K.¹,Christov Valerij Ch.¹

Affiliation:

1. Department of Chemistry, Faculty of Natural Sciences , Konstantin Preslavsky University of Shumen , 115 Universitetska Str., BG-9712 Shumen , Bulgaria

Abstract

Abstract An efficient method for regioselective synthesis of 5-(dimethoxyphosphoryl)-allenecarboxylates by an atom economical [2,3]-sigmatropic rearrangement of the mediated 3-(dimethoxyphosphanyloxy)-alk-4-ynoates is described. Alkyl 5-(dimethoxyphosphoryl)-alka-3,4-dienoates can be readily prepared via reaction of alkyl 3-hydroxy-alk-4-ynoates with dimethylchlorophosphite in the presence of a base. Alkyl 3-hydroxy-alk-4-ynoates were prepared by reaction of the metallated acetylenes with commercialy available alkyl 3-oxoalkanoates.

Publisher

Walter de Gruyter GmbH

Link

https://www.sciendo.com/pdf/10.2478/asn-2020-0029

Reference18 articles.

1. [1] (a) Patai, S., Ed. The Chemistry of Ketenes, Allenes and Related Compounds; John Wiley & Sons: New York, 1980; (b) Landor, S. R. Ed. The Chemistry of the Allenes; Academic Press: London, 1982, Vol. 1-3; (c) Pasto, D. J. Tetrahedron1984, 40, 2805-2827; (d) Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley & Sons: New York, 1988; (e) Zimmer, R. Synthesis1993, 165-178; (f) Elsevier, C. J. Methods of Organic Chemistry (Houben-Weyl); Vol. E21a, Helmchen, R.W.; Mulzer, J.; Schaumann, E., Eds., Thieme: Stuttgart, 1995, 537-566; (g) Krause, N.; Hashmi, A. S. K., Eds. Modern Allene Chemistry; Wiley-VCH: Weinheim, 2004, Vol. 1 & 2; (h) Brummond, K. M.; DeForrest, J. E. Synthesis2007, 795-818.

2. [2] (a) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev.2002, 31, 12-21; (b) Petrov, P. Y.; Angelov, C. M.; Petrov, G.; Alexiev, A.; Cavell, R. G. Heteroatom Chem.2004, 15, 413-417; (c) Ma, S. Aldrichimica Acta2007, 40, 91-102; (d) Hassan, H. H. A. M. Curr. Org. Synth.2007, 4, 413-439; (e) Petrov, P. Y.; Angelov, C. M.; McDonald, R.; Alexiev, A.; Cavell, R. G. Heteroatom Chem.2010, 21, 196-202; (f) Back, T. G.; Clary, K. N.; Gao, D. Chem. Rev.2010, 110, 4498-4553;

3. [3] (a) Bestmann, H. J.; Hartung, H. Angew. Chem. Int Ed.1963, 2, 214-215; (b) Aksnes, G.; Froeyen, P. Acta Chim. Scand.1968, 22, 2347-2347; (c) Lang, R. W.; Hansen, H. -J. Helv. Chim. Acta1980, 63, 438-455.

4. [4] Fillion, H.; Hseine, A.; Pera, M. -H.; Dufaud, V.; Refouvelet, B. Synthesis1987, 708-709.

5. [5] Tanaka, K.; Otsubo, K.; Fuji, K. Synlett1995, 933.