320716-52-7Relevant academic research and scientific papers
Additions of enantioenriched alenylzinc and indium reagents to lactic aldehyde ethers
Marshall,Chobanian
, p. 8357 - 8360 (2007/10/03)
Allenylzinc and indium reagents were generated in situ through Pd(0)-catalyzed metalation of (R)- and (S)-3-butyn-2-ol methanesulfonate with Et2Zn and InI. These reagents add to the benzyl and TBS ethers of (S)-lactic aldehyde to afford diastereomeric stereotriads in moderate to high yield. The (S)/(S) combination afforded the anti,anti adducts with 94:6-100:0 diastereoselectivity. The (R)/(S) combination was mismatched, affording a mixture of anti,syn and syn,anti adducts in diastereomeric ratios of ca. 80:20-85:15. Addition of the racemic allenylmetal reagents to the (S)-lactic aldehyde ethers afforded the products of matched and mismatched pairings in equal amount.
