Chemical process for the preparation of intermediates to obtain N-formyl hydroxy-lamine compounds

A process for preparing a compound of formula (VIII)

• comprising Step A:
• contacting a compound of formula (I)
• with a compound of the formula (II)
• Y—O—NH2 (II)
• in a suitable solvent under conditions suitable to form a compound of the formula (III)
• followed by asymmetric hydrogenation Step B:
• contacting the compound of formula (III) with hydrogen in the presence of a chiral ligand and a catalytic amount of a hydrogenation catalyst in a suitable solvent and under conditions suitable to form a compound of the formula (IV)
• followed by Step C:
• contacting the compound of formula (IV) with a base such as a Grignard reagent in a suitable solvent under conditions suitable to form a compound of the formula (V)
• followed by Step D:
• contacting the compound of formula (V) with a compound of the formula (VI)
• in a suitable solvent, optionally in the presence of an activator under conditions suitable to form a compound of the formula (VII)
• followed by Step E:
• contacting the compound of formula (VII) with a formylating agent in a suitable solvent under conditions suitable to form the compound of formula (VIII):
• wherein
• X is —CH2—, —S—, —CH(OH)—, —CH(OR)—, —CH(SH)—, —CH(SR)—, —CF2—, —C═N (OR)— or —CH(F)—;
• Y is a hydroxyl-protecting group;
• R is alkyl;
• R1 is aryl or heteroaryl;
• Ac is acetyl;
• each of R2, R3, and R10 independently is hydrogen or alkyl, or (R2 or R3) collectively form a C4-C7cycloalkyl;
• and
• n is 0-3, provided that when n is 0, X is —CH2—.