✦ LIBER ✦

Versatile, high 2,4-syn dialkyl diastereoselection in the radical debromination of α-bromo-α-methyl-δ-valerolactones with tri-n-butyltin hydride and a catalytic amount of triethylborane

✍ Scribed by Syun-ichi Kiyooka; Yong-Nan Li; Kazi A Shahid; Momotoshi Okazaki; Yoshihiro Shuto

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 71 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01507-6

No coin nor oath required. For personal study only.

✦ Synopsis

An interesting 2,4-syn dialkyl diastereoselection has been observed in the radical debromination of a-bromo-a-methyld-valerolactones. The reaction of 4-alkyl-2-bromo-3-hydroxy-2-methyl-5-pentanolides with Bu 3 SnH and a catalytic amount of Et 3 B gave, essentially, a single diastereomer with a 2,4-syn dialkyl relationship, independent of the orientation of the hydroxy substituent at C-3.

📜 SIMILAR VOLUMES

ChemInform Abstract: Versatile, High 2,4

ChemInform Abstract: Versatile, High 2,4-syn Dialkyl Diastereoselection in the Radical Debromination of α-Bromo-α-methyl-δ-valerolactones with Tri-n-butyltin Hydride and a Catalytic Amount of Triethylborane.

✍ Syun-ichi Kiyooka; Yong-Nan Li; Kazi A. Shahid; Momotoshi Okazaki; Yoshihiro Shu 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views