223429-01-4

Upstream product

• 223428-95-3 (1S,2R,4S,6S,7R)-4-Formyl-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decane-5-carboxylic acid tert-butyl ester 
• 931-50-0 cyclohexylmagnesium bromide 

Downstream Products

• 223429-11-6 (1S,2R,4S,6S,7R)-4-((S)-Benzoyloxy-cyclohexyl-methyl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decane-5-carboxylic acid tert-butyl ester 
• 223429-17-2 (S)-1-cyclohexyl-2-oxoethyl benzoate 

Relevant academic research and scientific papers

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

Diastereomerically pure 2-formyl-N-Boc-1,3-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 α-hydroxy aldehydes 11, which were immediately reduced to the corresponding 1,2-diols 12.