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A novel chiral synthetic equivalent of glyoxal and its application to the asymmetric synthesis of O-protected α-hydroxy aldehydes

✍ Scribed by Lino Colombo; Marcello Di Giacomo

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
214 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Diastereomerically pure 2-formyl-N-Boc-l,3-oxazolidine 7 was prepared in 83% yield from stannyloxazolidine 4. Grignard additions to the formyl group of compound 7 in the presence of Lewis acids afforded diastereomerically pure secondary carbinols 8. Protection of the hydroxyl group and unmasking of the oxazolidine ring gave O-protected ct-hydroxy aldehydes 11, which were immediately reduced to the corresponding 1,2-diols 12.

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