Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive

• Joachim E. Klee and
• Uwe Lehmann

Beilstein J. Org. Chem. 2010, 6, 766–772, doi:10.3762/bjoc.6.95

• Joachim E. Klee Uwe Lehmann Dentsply De Trey, De-Trey-Str. 1, 78467 Konstanz, Germany 10.3762/bjoc.6.95 Abstract Novel hydrolysis stable 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers 3 with phosphoric acid moieties were synthesized by a three step synthesis via Baylis–Hillman reaction of ethyl

• , comprising of phosphoric acid ester moieties, were synthesized via a three step synthesis via Baylis–Hillman reaction of ethyl acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using POCl3 (Scheme 1, Table 1). The double bonds in 3 are evident in

• -phosphonooxy-2-oxaalkyl)acrylate monomers 3 with phosphoric acid moieties and alkyl as well as oxyalkyl spacers were synthesized in three steps via Baylis–Hillman reaction of ethyl acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using POCl3. The

Recent progress on the total synthesis of acetogenins from Annonaceae

• Nianguang Li,
• Zhihao Shi,
• Yuping Tang,
• Jianwei Chen and
• Xiang Li

Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48

Sordarin, an antifungal agent with a unique mode of action

• Huan Liang

Beilstein J. Org. Chem. 2008, 4, No. 31, doi:10.3762/bjoc.4.31

• reaction leading to a series of tricyclic analogs 85 displaying various functional groups. The C-10 ketone in this material would enable annulation sequences leading to tetracyclic compounds 84. The precursor to 85, intermediate 86, would arise from a Baylis-Hillman reaction [48] between aldehyde 87 and

Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds

• G. K. Surya Prakash,
• Xiaoming Zhao,
• Sujith Chacko,
• Fang Wang,
• Habiba Vaghoo and
• George A. Olah

Beilstein J. Org. Chem. 2008, 4, No. 17, doi:10.3762/bjoc.4.17

• the terminal position of the double bond due to steric effects. On the basis of the above mentioned results, a proposed mechanism for the formation of 5a–h is outlined in Scheme 1. Trialkylphosphine catalysed Morita-Baylis-Hillman reaction is well studied by a number of groups [37][38][39]. Addition

Asymmetric aza-Diels- Alder reaction of Danishefsky's diene with imines in a chiral reaction medium

• Bruce Pégot,
• Olivier Nguyen Van Buu,
• Didier Gori and
• Giang Vo-Thanh

Beilstein J. Org. Chem. 2006, 2, No. 18, doi:10.1186/1860-5397-2-18

• simplicity in their preparation, their recyclabilities and their unique properties.[23][24] Thus, we were the first to promote the use of chiral ILs as the only source of chirality in the asymmetric Baylis-Hillman reaction.[25] Ee's of up to 44% were obtained using ephedrinium-based ILs.[26] Two further

• applications of chiral ILs in the asymmetric induction were reported in 2005 by Armstrong[27] and Bao.[28] Recently, Leitner and coworkers reported a highly enantioselective aza-Baylis-Hillman reaction (up to 84% ee) by using an IL with chiral anion, derived from (-)-malic acid, as the sole source of chirality

• related Baylis-Hillman reaction between p-nitrobenzaldehyde and methyl acrylate using the above chiral IL.[25] A slight increase in de (not optimized value) was detected when employing p-methoxyphenyl (Table 3, entry 2, R = p-MeOC6H4). ILs are highly recyclable and do not lose any of their properties even