Journal
TETRAHEDRON-ASYMMETRY
Volume 26, Issue 1, Pages 53-66Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2014.12.001
Keywords
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Funding
- MICINN
- MEC
- MINECO
- FEDER program [CTQ2011-27705]
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The extension of the diastereoselective functionalization of the Ph2P group of C-chiral P,P-diphenyl phosphinimidic amides via directed ortho-lithiation (DoLi)-electrophilic quench reactions as a method for the preparation of structurally diverse P-stereogenic compounds is described. Transformations at both the phosphorus-containing and the ortho-functional groups provide access to a large variety of P-stereogenic derivatives with excellent stereocontrol. These transformations include aza-Wittig reactions, N-alkylations, methanolysis, nucleophilic displacements with Grignard reagents, phosphine oxide reductions, azide to amine conversions, halogen/metal exchange, and Suzuki cross-coupling and condensation reactions. These transformations increase the diversity of functional groups at the ortho-disubstituted phenyl ring and enable the synthesis of enantiopure ortho-formyl- and ortho-stannyl-phosphinic amides that are difficult to prepare by other methods. The new products synthesized might be used as building blocks for the construction of high value added P-stereogenic compounds. This is illustrated by the synthesis of [1,5,2]diazaphosphinin-6(5H)-one 21, a phosphazenylphosphinate (S-PN,R-PO)-22 and the analogues of relevant bidentate and tridentate privileged structures such as PHOX-like 23 and the heteroatomic N,O,P-tridentate ligand 25. (C) 2014 Elsevier Ltd. All rights reserved.
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