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30.6.3.6 Transition-Metal-Catalyzed Tandem Allylation–Cyclization

DOI: 10.1055/sos-SD-130-00273

Mutoh, Y.Science of Synthesis Knowledge Updates, (20183413.

Pyrroloindolines (hexahydropyrrolo[2,3-b]indoles) are also prepared by transition-metal catalysis, involving C3 allylation of tryptamines and subsequent cyclization of an imine moiety. Palladium/(S,S)-22 complex effectively catalyzes the allylation of tryptamines 23 with allyl alcohol, which is followed by cyclization to give 5,5-fused N,N-acetal skeletons 24 (Scheme 7).[‌6‌]

Meeeee 8 Meeeeeeee-Meeeeeeee Meeeee MeeeeeeeeeMeeeeeeeeee[‌8‌]

Meeeeeeeeee 8

M8 ee (%) Meeee (%) Mee
M 88 88 [‌8‌]
MMe 88 88 [‌8‌]

Meeeeee eeeeeeeee eee eeeeeeeeeeee eeeee ee eeeeeee/eeeeeeeeeeeeeee eeeeeee. Meee, eeeeeee/88 eeeeeee eeeeeee eee eeeeeee eeeeeeeeeee/eeeeeeeeeee ee eeeeeeeeeee 88 eeee eeeeeee eeeeeeeee 88 ee eee eeeeeeee ee eeeeeeeeeeeeee eee eeeeeeeee eeee-eeeeeeee ee eee eeeeeeeee, eee eee eeeeeeeeeeeee eeeeeeeeeeeeeeee (±)-88 eee eeeeeeee eeee eeeeeeee/eeeeee eeeeeeeeeee ee >88:8 (Meeeee 8).[‌8‌] Me eeeee e eeeeee eeeeeee eeeeeee, eeeeeee eeee eeeeee­ee­eee(eeeeeeeee-8,8-eeeee)eeeeeeeee(M) eee eeeeeeeeeeeeeee (M,M)-88 ee eee eeeeeeee ee eeeeeeeee 88, ee eeeeeeeeeeeeeeee eeeeeeeeee/eeeeeeeeeee eeeeeee ee eeeeeeeeeee 88 eeee eeeeee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeee eeeeeee eeeeeee 88 eeee eeee eeeeeee- eee eeeeeeeeeeeeeeeeeeee (Meeeee 8).[‌8‌]

Meeeee 8 Meeeeee-Meeeeeeee Meeeee MeeeeeeeeeMeeeeeeeeee[‌8‌,‌8‌]

Meeeeeeeeee 8

M8 e Meeee (%) Mee
M 8 88 [‌8‌]
M 8 88 [‌8‌]
Me 8 88 [‌8‌]
M 8 88 [‌8‌]

M8 M8 ee (%) ee Meeee (%) Mee
M Me 88 >88:8 88 [‌8‌]
M Mee 88 >88:8 88 [‌8‌]
M Me 88 >88:8 88 [‌8‌]

Meeeeeeeeeee Meeeeeeee

eeee-Meeee (8eM,8eM)-8e-Meeee-8,8e,8,8e-eeeeeeeeeeeeeeeee[8,8-e]eeeeee-8(8M)-eeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌8‌]

8-Meeee-8-MMM eee eeeeeeee ee eeeeeee: e 8-eM eeeee-eeeeeeee eeeee eee eeeeeee eeee 8-MMMM (88.8ee, 8.888eeee), eee eee eeeee eee eeeeeee eeee M8. Me eeee eee eeeee MMM (888 µM), eeeeeeee ee eee-8-eee (88 µM, 8.88eeee, eeeeeeeee eeee eeeeee), eee eee eeeeeee eee eeeeeee ee ee eee 8e.

M eeeeeeee eeeee eee eeeeeee eeee Me8(eee)8MMMe8 (8.88ee, 8.888eeee), (M,M)-88 (88.8ee, 8.888eeee), eee eeeeeee 88 (8.8eeee), eee eee eeeee eee eeeeeee eeee M8. Me eee eeeee eee eeeee eee MM8Me8 (8eM, eeeeeeee ee eeeeeeeeeeeeee), eee eee eeeeeee eee eeeeeee eee 88eee eeeeee eee 8-eeeee-8-MMM eeee (8.888eeee) eee eeeee. Mee eeeeeeee eeeeeee (eeeeeeeeee) eee eeeeeee eee e eeeeeee 8eee eee eeeeeee ee eeee ee 8°M. Me eeee eee eeeee eeeeeeee eeeee eeeeeee (88 µM, 8.8eeee), eee eee eeeeeeeee eeee eee eeeeeee ee 8°M eee 88e. Mee eeeeeeeee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eeeee ee ee MMM (8eM). Me eee MMM eeee eee eeeee 8-eeeeeeeeee-8-ee (88 µM, 8eeee), eee eee eeeeeee eee eeeeeee eee 8e. Mee eeeeeeeee eeeeeee eee eeeeeeee, eee eee eeeeee eeee eeeeee eeee MeMMe (88eM). Mee eeeeeeee eee eeeeee eeee eee. ee Me8MM8 (8 × 8eM) eee eeeee (8eM), eee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe) ee eeee eee eeeeeeee 88.

(8eM*,8eM*)-8e-(8-Meeeeeeee-8-ee-8-ee)-8-eeeee-8,8,8,8e,8,8e-eeeeeeeeeeeeeeee[8,8-e]eeeeeee 88 (e=8) eee (8eM*,8eM*)-8e-(8-Meeeeeeee-8-ee-8-ee)-8-eeeee-8,8,8,8e,8,8e-eeeeeeeee-8M-eeeeee[8,8-e]eeeeeee 88 (e=8); Meeeeee Meeeeeeee:[‌8‌]

Me e eeeee-eeeee, 88-eM Meeeeee eeeee eeeeeeee eeee e eeeeeee eee eeee eeeee eeeeeee 88 (8.88eeee, 8.88eeeee) eee e-MeMM (888ee, 8.88eeee, 8.88eeeee, eeeeee eee eeeeeee eeeee eee). Mee eeeee eee eeeeee eeee e eeeeee, eeeeeeeee eee eeee-eeeeee eeee M8 (8 ×). Me eeee eeee eeeee 8.8M Me8M ee MMM (8.8eM, 8.8eeee, 8.8eeeee) eee 8,8-eeeeeee (8.8eM) ee 88°M, eee eee eeeeeeeee eeeeeee eee eeeeeee ee eeee eeeeeeeeeee eee 88eee eeeeee e 8,8-eeeeeee (8.88eM) eeee ee {MeMe(eee)}8 (8.8ee, 8.8 µeee, 8.88eee%) eee eeeeeeeeeeeeeee 88 (8.8ee, 8.8 µeee, 8.88eee%) (eeeeeeee ee e eeeee-eeeeee eeee, eeeeeee eeee M8 eee eeeeeee ee 88°M eee 88eee eeeee ee eee eeeeeeee) eee eeeee eee Meeeeee eeeee eeeeeee e eeee ee M8. Me eee eeeeeee eeeeeee eee eeeee eeeeeee eeeeeeeee 88 (888 µM, 888ee, 8.88eeee, 8.88eeeee) eee eeeeeee, eee eee eeeeeee (eeeee eeeeee e eee, eeeee eeeeee eeeeee eeeeee eeeee) eee eeeeeee ee 88°M eee 88e. Me eee eeeeeeeee eeeeeee eee eeeee Me8M (8eM) eee eee. ee MM8Me (8eM), eeeeeeeeeeee. Me eeee eee eeeee eeeeeeeee M8M (8eM), eee eee eeeeeee eeee eee eeeeee eeee eee. ee MeMe (88eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee eeeeeeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee), eee eee eeeeeee (±)-88 eee eeeeeeee ee e eeeeee eeeeeeeeeeee. Mee eeeeeeeeeeeeeeee (eeeeeeee/eeeeee) eee eeeee ee ee >88:8 ee 8MMMM eeeeeeee ee eee eeeee eeeeeee.

(8eM,8eM)-8e-[(M)-8-Meeeeeeeeee]-8,8,8,8e,8,8e-eeeeeeeeeeeeeeee[8,8-e]eeeeee 88; Meeeeee Meeeeeeee:[‌8‌]

M eeeee-eeeee Meeeeee eeee eee eeeeee ee ee eee eeeeee eeee eeeee. Me eeee eeee eeeee {MeMe(eee)}8 (8.8ee, 8.888eeee, 8.8eee%), (M,M)-88 (8.8ee, 8.888eeee, 8.8eee%), 8,8,8-eeeeeeeeeeeee[8.8.8]eee-8-eee (88; 8.8ee, 8.88eeee, 88eee%), eee MMM (8.8eM). Mee eeeeeee eee eeeeeee ee ee eee 88eee, eeeeee ee eeeeee eeee. Me eeeeeee Meeeeee eeee eeee eeeee eeeeee eeeeeeeeee 88 (8.8eeee, 8eeeee), eeeeee eeeeeeee eeeeeeeee (8.88eeee, 8eeeee), Me8M (88.8ee, 8.88eeee, 8eeeee), eee MMM (8eM). Me eeee eee eeeee eee eeeeee eeeeeeee eeee, eee eee eeeeeee eee eeeeeee ee ee eeeee eee eeeeee eeeeeeee eeeeeeeee eee eeeee eeeeeeee (MMM). Mee eeeeeeeee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee 8MMMM ee eeeeeeee eee eeeee ee eeeeeeee/eeeeee eee eeeeeeeeeeeeeeeeeeee ee 88. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8) ee eeeeee eee eeeeeee eeeeeee 88.

References


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