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2.11.3.2.2.2 Using a Cinchona Alkaloid

DOI: 10.1055/sos-SD-202-00255

Bergin, E.Science of Synthesis: Stereoselective Synthesis, (20112580.

A very useful procedure has been developed for the hydrophosphonylation of N-hetarylsulfonyl-protected imines 75 to α-aminophosphonates 76 (Scheme 40).[‌71‌] The reaction is quite specific for the cases where the N-arylsulfonyl group is a heterocycle with a nitrogen in the 2-position (pyridine and quinoline have been employed), presumably because of some coordination between the protecting group and the catalyst. The sulfonyl group can be introduced by the condensation of the sulfonamide and aldehyde using titanium(IV) chloride as a Lewis acid as reported previously.[‌72‌]

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M8 Meeeeeeee Meee (°M) eee (%) Meeee (%) Mee
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8-MeM8M8 88 88 88 (88) >88 [‌88‌]
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References


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