152940-87-9

Upstream product

• 141-75-3 butyryl chloride 
• 152940-94-8 (3S,5R)-5-(benzoyloxy)-2,2,6,6-tetramethylheptan-3-ol 
• 630-19-3 pivalaldehyde 
• 106594-89-2 erythro 2,2,6,6-tetramethyl 3,5-heptanediol 
• 42052-53-9 5-hydroxy-2,2,6,6-tetramethyl-3-heptanone 
• 75-97-8 3,3-dimethyl-butan-2-one 

Relevant academic research and scientific papers

Conformationally rigid acyclic 2,2,6,6-tetramethyl-3,5-heptanediol (TMHDiol) derivative as a new class of chiral auxiliaries

As a new chiral auxiliary, a 2,2,6,6-tetramethyl-3,5-heptanediol (TMHDiol) derivative has been developed. This chiral auxiliary is an acyclic, but strongly conformationally biased, molecule. Conjugate addition of lithium TV-benzyl-W-(trimethylsilyl)amide (LSA) to the enoates having a TMHD auxiliary proceeded with high diasteroselectivities to give β-amino esters in high yields, although the use of conventional auxiliaries such as 8-phenylmenthyl and oxazolidone resulted in low diastereoselectivity. Organocopper conjugate addition to TMHD crotonate, heptanoate, and cinnamate produced high diastereoselectivities, and Diels-Alder reaction of TMHD acrylate with cyclopentadiene in the presence of TiCl4 afforded an endo adduct exclusively with high diasteroselectivity. The addition of LSA proceeded via an s-cis conformation of enoates, but the organocopper addition in the presence of BFOEt3· and the Diels-Alder reaction in the presence of TiCl4 proceeded through an s-trans form.