Ammonium ylides for the diastereoselective synthesis of glycidic amides.
نویسندگان
چکیده
A highly trans-selective protocol for the synthesis of glycidic amides was developed. This approach gave access to oxiranes by reacting stabilised ammonium ylides bearing an α-carbonyl group and aromatic aldehydes in moderate to good yields.
منابع مشابه
Identification of the best-suited leaving group for the diastereoselective synthesis of glycidic amides from stabilised ammonium ylides and aldehydes.
In comparison to the use of sulfur ylides, the use of ammonium ylides for the synthesis of epoxides is significantly less developed. As a part of our systematic investigations concerning the use of amide-stabilised ammonium ylides for the synthesis of glycidic amides we have focused on the identification of the best-suited amino leaving group for this purpose. Whereas tertiary amines like quinu...
متن کاملAmmonium ylides for the diastereoselective synthesis of glycidic amidesw
The (dia-)stereoselective synthesis of glycidic amides and esters has attracted considerable interest over the last few decades mainly due to the high potential of these compounds as synthetically useful intermediates in a variety of organic syntheses. Ylides have proven to be very powerful synthons for the formation of epoxides providing alternatives to the oxidation of a,b-unsaturated carbony...
متن کاملAsymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides† †Electronic supplementary information (ESI) available: Experimental and computational details, characterization of new compounds, and copies of NMR spectra. CCDC 1023711 and 1030561. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ob02318h Click here for additional data file. Click here for additional data file.
The use of carbonyl-stabilised ammonium ylides to access chiral glycidic amides and the corresponding aziridines has so far been limited to racemic trans-selective protocols. We herein report the development of an asymmetric approach to access such compounds with high levels of stereoselectivity using easily accessible chiral auxiliary-based ammonium ylides. The use of phenylglycinol as the chi...
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A highly enantio- and diastereoselective [4+1] annulation between in situ generated ammonium ylides and o-quinone methides for the synthesis of a variety of 2,3-dihydrobenzofurans has been developed. The key factors controlling the reactivity and stereoselectivity were systematically investigated by experimental and computational means and the energy profiles obtained provide a deeper insight i...
متن کاملHighly diastereoselective synthesis of 3-hydroxy-2,2,3-trisubstituted indolines via intramolecular trapping of ammonium ylides with ketones.
A Rh2(OAc)4-catalyzed diazo decomposition reaction of diazo esters with 2-aminophenyl ketones is reported. A series of 3-hydroxy-2,2,3-trisubstituted indolines are produced in good yields with excellent diastereoselectivities via an intramolecular aldol-type trapping of ammonium ylides with ketone units.
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ورودعنوان ژورنال:
- Chemical communications
دوره 47 7 شماره
صفحات -
تاریخ انتشار 2011