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Stereodivergent allylindation of cyclopropenes. Remarkable stereodirection and acceleration by neighbouring carboxyl and hydroxyl groups

✍ Scribed by Shuki Araki; Hiroyuki Nakano; Kandasamy Subburaj; Tsunehisa Hirashita; Kensuke Shibutani; Hatsuo Yamamura; Masao Kawai; Yasuo Butsugan

Book ID
108386968
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
248 KB
Volume
39
Category
Article
ISSN
0040-4039

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ChemInform Abstract: Stereodivergent All
ChemInform Abstract: Stereodivergent Allylindation of Cyclopropenes. Remarkable Stereodirection and Acceleration by Neighboring Carboxyl and Hydroxyl Groups.
✍ S. ARAKI; H. NAKANO; K. SUBBURAJ; T. HIRASHITA; K. SHIBUTANI; H. YAMAMURA; M. KA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB

The allylindation of cyclopropenes (I) is found to depend remarkably on the nature of the substituent at the α-carbon. Thus, a hydroxymethyl and carboxyl group direct to the cis products (III) based on intramolecular chelation, whereas acetoxymethyl and ester groups direct to trans products (IV) due