69489-16-3

Upstream product

• 168961-30-6 (1S,2R,4S,6S,7R)-4-((S)-1-Hydroxy-2-methyl-1-phenyl-propyl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decane-5-carboxylic acid tert-butyl ester 
• 51559-18-3 (S)-(-)-3-methyl-2-phenylbutane-1,2-diol 
• 81968-50-5 2-methyl-1-(2-phenyl-hexahydro-pyrrolo[1,2-c]imidazol-3-yl)-propan-1-one 

Downstream Products

• 51559-18-3 (S)-(-)-3-methyl-2-phenylbutane-1,2-diol 

Relevant academic research and scientific papers

Camphor-derived 2-stannyl-N-Boc-1,3-oxazolidine: A new chiral formylanion equivalent for the asymmetric synthesis of 1,2-diols

Optically pure 2-tributylstannyl-N-Boc-1,3-oxazolidine 6, prepared from the camphor-derived aminoalcohol 5, was converted to diastereomerically pure 2-acyl derivatives 8 in three steps. Reaction of these ketones with Grignard reaagents at -78°C proceeded with high stereoselectivity affording tertiary carbinols which gave 1,2-diols with >96% ee after hydrolysis and reduction of the intermediate α-hydroxy aldehydes. A new deblocking procedure of the t-Boc group is also described.

α-Hydroxyaldehyde and a process for preparing the same

An optically active or racemic α-hydroxyaldehyde represented by the general formula (2), STR1 wherein R1 represents a C6 -C14 aryl group, C1 -C10 alkyl group, C3 -C10 alkenyl group, C2 -C10 alkynyl group, C7 -C14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R2 represents a C1 -C10 alkyl group, C2 -C10 alkenyl group, C2 -C10 alkynyl group, C7-C14 aralkyl group, C6 -C14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), STR2 (wherein A represents a C6 -C14 aryl group or a C1 -C4 alkyl or alkoxy group- or halogen-substituted C6 -C14 aryl group and R1 is as defined above) to react with a Grignard reagent, and thereafter hydrolyzing the reaction product.

ASYMMETRIC SYNTHESIS BASED ON CHIRAL DIAMINES HAVING PYRROLIDINE RING

Various highly stereoselective asymmetric reactions based on chiral diamines having pyrrolidine ring are described.Some of these reactions have been successfully applied to the syntheses of natural products.