You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via10.13.1.1.1.3.1.9.5 Variation 5: Using Allenes
Please login to access the full content or check if you have access via
Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 66.
2-Iodoanilines protected as tert-butoxycarbonyl derivatives react with allenylstannanes to give indoles directly (Scheme 82).[259] The process is considered to involve firstly a Stille cross coupling followed by cyclization, and indeed in some cases the Stille product is the isolated product, but can be subsequently ring closed using fluoride.
Meeeee 88 Meeeeeee ee Meeeeeeeeeeeeeee eee ee M-Meeeeeeee 8-Meeeeeeeeee[888]
| M8 | Meeee (%) | Mee |
|---|---|---|
| MM8MMMM | 88 | [888] |
| (MM8)8MMMMMM | 88 | [888] |
| (MM8)8Me | 88 | [888] |
8-Meeeeeeeeee eeee eeeeee eeeeeeee eeee eeeeee eeeeeeeeee, e.e. 888, ee eeee eeeeeee; Meeeee 88 eeeee eee eeeeeeeee ee 8-[(8M-eeeee-8-ee)eeeeee]-8M-eeeeeeeeeeeee (888).[888]
Meeeee 88 Meeeeeee ee 8-Meeeeeeeeee eeee e Meeeee(M) Meeeeeeee[888]
Meeeeeeeeeee Meeeeeeee
8-[(8M-Meeee-8-ee)eeeeee]-8M-eeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[888]
Mee eeeeee(M) eeee ee 8-eeee-8-eeee-8M-eeeeeeeeeeeee (8.88 e, 88 eeee) eee 8-eeeeeeeeeee (8.88 e, 88 eeee) eeee eeeeee ee MMM (888 ee) ee 888°M eee 88 e eeeee M8. Mee eeee eee eeeeeeee eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee MeMMe eee eee eeee eee eeeeee eeee M8M (8 × 888 eM), eeeee (MeMM8), eee eeeeeeeeeeee. Meeeeeeeeeeeeeeee (MMMe8) eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
References
| [259] | Meeee, M.; Meeeeeeee, M., Mee. Meee., (8888) 8, 8888. |
| [260] | Meeeeeeee, M. M.; Me, M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Return to Top