✦ LIBER ✦

Reductive 1,2-Allylboration of Indoles by Triallyl- and Triprenylborane − Synthesis of 2-Allylated Indolines

✍ Scribed by Yury N. Bubnov; Ilya V. Zhun'; Elena V. Klimkina; Anatoly V. Ignatenko; Zoya A. Starikova

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 265 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200010)2000:19<3323::aid-ejoc3323>3.0.co;2-k

No coin nor oath required. For personal study only.

✦ Synopsis

Indoles undergo reductive α-allylation upon treatment with allylic boranes (triallyl-and triprenylborane) to give, after deboronation, the corresponding 2-allylated indolines in 70-85% yield. 1,2-Addition of the allylboron fragment to heterocycles occurs with full rearrangement of the allylic moiety. Reductive prenylboration of 3-substituted indoles, as well as allylboration of 3-isopropylindole, with All 3 B proceed stereoselectively to produce trans-2,3-disubstituted indolines only, while similar reactions of triallylborane with 3-R-indoles,

📜 SIMILAR VOLUMES

ChemInform Abstract: Reductive 1,2-Allyl

ChemInform Abstract: Reductive 1,2-Allylboration of Indoles by Triallyl- and Triprenylborane — Synthesis of 2-Allylated Indolines.

✍ Yury N. Bubnov; Ilya V. Zhun'; Elena V. Klimkina; Anatoly V. Ignatenko; Zoya A. 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 29 KB 👁 2 views

ChemInform Abstract: Synthesis of Indole

ChemInform Abstract: Synthesis of Indole Derivatives by (2 + 2) Photocycloaddition of Indoline-2-thiones with Alkenes and Photodesulfurization of Indoline-2- thiones.

✍ T. NISHIO; M. OKA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 1 views

Synthesis of 2-Alkylidenepyrrolidines, P

Synthesis of 2-Alkylidenepyrrolidines, Pyrroles and Indoles by Condensation of Silyl Enol Ethers and 1,3-Bis-Silyl Enol Ethers with 1-Azido-2,2-dimethoxyethane and Subsequent Reductive Cyclization.

✍ Esen Bellur; Helmar Goerls; Peter Langer 📂 Article 📅 2005 🏛 John Wiley and Sons ⚖ 39 KB 👁 1 views

Synthesis of 2-Alkylidenepyrrolidines, P

Synthesis of 2-Alkylidenepyrrolidines, Pyrroles and Indoles by Condensation of Silyl Enol Ethers and 1,3-Bis-Silyl Enol Ethers with 1-Azido-2,2-dimethoxyethane and Subsequent Reductive Cyclization.

✍ Esen Bellur; Helmar Goerls; Peter Langer 📂 Article 📅 2005 🏛 John Wiley and Sons ⚖ 36 KB 👁 1 views

ChemInform Abstract: Palladium-Catalyzed

ChemInform Abstract: Palladium-Catalyzed Synthesis of Indoles by Reductive N-Heteroannulation of 2-Nitrostyrenes.

✍ B. C. SOEDERBERG; J. A. SHRIVER 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB

ChemInform Abstract: Synthesis of 2-Meth

ChemInform Abstract: Synthesis of 2-Methylindoline- and 2-Methyl-1,2,3,4-tetrahydroquinoline-Derived Phosphoramidites and Their Applications in Iridium-Catalyzed Allylic Alkylation of Indoles.

✍ Wen-Bo Liu; Hu He; Li-Xin Dai; Shu-Li You 📂 Article 📅 2009 🏛 John Wiley and Sons ⚖ 35 KB