169330-79-4

Upstream product

• 100-46-9 benzylamine 
• 3070-53-9 1,6-heptadiene 
• 204120-10-5 1,7-Bis-(tert-butyl-dimethyl-silanyloxy)-heptane-2,6-diol 
• 5581-23-7 Heptane-1,2,6,7-tetraol 
• 204120-11-6 C₃₃H₅₆O₈S₂Si₂ 

Downstream Products

• 169870-40-0 ((2R,6R)-1-Benzyl-6-hydroxymethyl-piperidin-2-yl)-methanol 
• 204120-15-0 (2R,6R)-1-Benzyl-2,6-bis-methoxymethoxymethyl-piperidine 

Relevant academic research and scientific papers

Symmetry-Assisted Synthesis of C2-Symmetric trans-α,α'-Bis(hydroxymethyl)pyrrolidine and -piperidine Derivatives via Double Sharpless Asymmetric Dihydroxylation of αω-Terminal Dienes

A new strategy has been developed for the synthesis of C2-symmetric trans-α,α'-bis(hydroxymethyl)pyrrolidine and piperidine derivatives 1-3 starting from symmetric αω-terminal dienes 4-6. The double-asymmetric dihydroxylation (AD) reaction of 4-6 gave C2-symmetric tetrols, which were converted in a four-step sequence to C2-symmetric azacycloalkanes 17,9, and 22, respectively. These azacycloalkanes were transformed into 1-3 in high enantiomeric excess (82% → 98%ee). The double AD reaction proved to cause enantiomeric enhancement, even though the asymmetric induction for the first AD reaction is moderate. In addition, it was observed that the chromatography on silica gel of several C2-symmetric azacycloalkanes (17, 20, and 22) of varying ee's resulted in marked enantiomeric fractionation.

New entry to C2 symmetric trans-2,6-bis(hydroxymethyl)-piperidine derivatives via the Sharpless asymmetric dihydroxylation

A new synthesis of both enantiomers of C2-symmetric trans-2,6-bis(hydroxymethyl)piperidine derivatives 1 by the use, as a key reaction, of the Sharpless asymmetric dihydroxylation of a symmetric diene 2 is presented.