@article { ISI:000303497600030,
	title = {Enantiomerically Pure Phosphaalkene-Oxazolines (PhAk-Ox): Synthesis, Scope and Copolymerization with Styrene},
	journal = {CHEMISTRY-A EUROPEAN JOURNAL},
	volume = {18},
	number = {20},
	year = {2012},
	month = {MAY},
	pages = {6349-6359},
	abstract = {{The design of a synthetic route to a class of enantiomerically pure phosphaalkeneoxazolines (PhAk-Ox) is presented. The condensation of a lithium silylphosphide and a ketone (the phospha-Peterson reaction) was used as the P?C bond-forming step. Attempted condensation of PhC(?O)Ox (Ox=CNOCH(iPr)CH2) and MesP(SiMe3)Li gave the unusual heterocycle (MesP)2C(Ph)?CN-(S)-CH(iPr)CH2O (3). However, PhAk-Ox (S,E)-MesP?C(Ph)CMe2Ox (1?a) was successfully prepared by treating MesP(SiMe3)Li with PhC(?O)CMe2Ox (52?\%). To demonstrate the modularity and tunability of the phospha-Peterson synthesis several other phosphaalkeneoxazolines were prepared in an analogous manner to 1?a: TripP?C(Ph)CMe2Ox (1?b; Trip=2,4,6-triisopropylphenyl), 2-iPrC6H4P?C(Ph)CMe2Ox (1?c), 2-tBuC6H4P?C(Ph)CMe2Ox (1?d), MesP?C(4-MeOC6H4)CMe2Ox (1?e), MesP?C(Ph)C(CH2)4Ox (1?f), and MesP?C(3,5-(CF3)2C6H3)C(CH2)4Ox (1?g). To evaluate the PhAk-Ox compounds as prospective precursors to chiral phosphine polymers, monomer 1?a and styrene were subjected to radical-initiated copolymerization conditions to afford {[}\{MesPC(Ph)(CMe2Ox)\}x\{CH2CHPh\}y]n (9?a: x=0.13n},
	issn = {0947-6539},
	doi = {10.1002/chem.201103887},
	author = {Dugal-Tessier, Julien and Serin, Spencer C. and Castillo-Contreras, Emmanuel B. and Conrad, Eamonn D. and Dake, Gregory R. and Gates, Derek P.}
}
