Single diastereomers of unsymmetrical tris-spirocyclic cyclotriphosphazenes based on 1,1'-bi-2-naphthol--synthesis and structures.
摘要：
Diastereoselective synthesis and characterization of chiral unsymmetrical tris-spirocyclic cyclotriphosphazenes based on chiral 1,1-bi-2-naphthol (BINOL) are reported. Specifically, the chiral compounds (-)N3P3[1,1-O2(C10H6)2](O-2,2C6H4-C6H4O)Cl2 [(-)- 4 ] and (-)N3P3[1,1-O2(C10H6)2](OCH2CH2NMe)2 [(-)- 5 ] are prepared by starting with the chiral mono-spiro compound (-)N3P3[1,1-O2(C10H6)2]Cl4 [(-)- 3 ]. Synthesis of four other chiral spirocyclics, N3P3[1,1-O2(C10H6)2](OCH2CH2 NMe)(O-2,2C6H4-C6H4O)[(-)- 6 and (+)- 6 ], N3P3[1,1-O2(C10H6)2](NMe2)4 [(-)- 7 ], N3P3[1,1-O2(C10H6)2](O-2,2C6H4-C6H4O)(NMeCH2CH2OH)2 [(-)- 8 and (+)- 8 ], and N3P3[1,1-O2(C10H6)2](O-2,2C6H4-C6H4O)[NHCH2CH2CH2Si(OEt)3]2 ( 9 ) is also reported herein. Compounds 4 - 6 are obtained in the solid state diastereoselectively and their X-ray structures have been determined and discussed. The diastereoselectivity is also shown by structural characterization of two distinct isomers in the case of 6 [(-)- 6 and (+)- 6 , respectively] by starting with precursor of 3 having ( R ) or ( S )-BINOL residue. The 1H NMR spectra of 7 and 8 exhibit doublets with virtual coupling for the methyl protons, consistent with the chiral nature of the binaphthoxy residue. The potential of 9 , which hydrolyzes readily in CDCl3 solution, as a useful precursor for chiral polymer applications is highlighted. Chirality, 2008. 2008 Wiley-Liss, Inc.
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DOI：
10.1002/chir.20528
被引量：
年份：
2010
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