Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 17
228
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Simple and Advantageneous Stereoselective Synthesis of (Z)-Allyl Phosphonates Starting from Baylis–Hillman Adducts

, &
Pages 2479-2489 | Received 01 Dec 2010, Published online: 29 May 2012
 

Abstract

Baylis–Hillman adducts 3-hydroxyl-2-methylene alkanoates have been converted in one pot into the corresponding (Z)-allyl phosphonates by treatment with FeCl3 and trialkyl phosphites in toluene under reflux. The products are formed in excellent yields (88–98%) within 1–1.5 h. The process is highly convenient and efficient, cost-effective, and remarkably stereoselective.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENT

The authors thank the Council of Scientific and Industrial Research, New Delhi, for financial assistance.

Notes

a Reaction conditions: Baylis–Hillman adduct, 1a (1 mmol), triethyl phosphite (1.2 mmol), Lewis acid (0.35 mmol), and toluene (10 ml) under reflux.

b Yields of isolated pure compound after column chromatography.

a Reaction conditions: Baylis–Hillman adduct, 1a (1 mmol), trialkyl/triphenyl phosphite (1.2 mmol), FeCl3 (0.35 mmol), and toluene (10 ml); the reaction mixture was stirred for 1 h under reflux.

b Yields of isolated pure compound after column chromatography.

a Reaction conditions: Baylis–Hillman adduct, 1 (1 mmol), triethyl phosphate (1.2 mmol), FeCl3 (0.35 mmol), and toluene (10 ml); the reaction mixture was stirred under reflux.

b R1 = Me and RII = Et in each entity otherwise stated.

c The products were characterized from their IR, 1H NMR, 13C NMR, and HRMS spectra.

d Yields of isolated pure compound after column chromatography.

Part 204 in the series, “Studies on novel synthetic methodologies.”

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.