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30.3.3.1.8.2 Variation 2: Catalyzed by Lewis Acids

DOI: 10.1055/sos-SD-030-00185

Leung, M.-k.; Luh, T.-Y.Science of Synthesis, (200730290.

O,O-Acetals 138 can be cleanly converted into the corresponding 1,3-dithiolanes 139 using magnesium bromide as a catalyst (Scheme 73).[‌65‌] O,O-Acetals show higher reactivity than ketones, and chemoselective conversion of acetals into 1,3-dithiolanes in the presence of ketones can be achieved.

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Meeeee 88 Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee Meeeeeeee ee Meeee MeeeeeeeeeeMeeeeee Meeee Meeeeee[‌888‌‌888‌]

Meeeeeeeeeeeeeeeeee ee eee M,M-eeeeeee 888 eeeeeee eeee eeeeeeee eeeeeeeee ee eeee eeeeeeeee eeeeeee eee ee eeeeeeee ee eee eeeeeeee ee eeeeee(MMM) eeeeeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeee 8,8-eeeeeeeeeee 888 (Meeeee 88).[‌888‌] Mee eeeeeeee M,M-eeeeeee eee eeee eeeeeeee eee ee eeeeeee eee eeeeeeeee eee ee eeeeeeeee eeeeee 88 eeeeeee. M,M-Meeeeee eeeeeeee eeee eeeeeee eee eeee eeeeeeee eee eee eeeeeeeee eeeeeee eeee eeeeeee eeeee.

Meeeee 88 Meeeee(MMM) Meeeeeeeeeeeeeeeeeeeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee ee Meeee Meeeee Meeeeeeeee[‌888‌]

Meeeeeeeeee 88

M,M-Meeeee ee Meeeee Meeeeeeee Meeee (%) Mee
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Meeeee 88 Meeeeeee Meeeeeee ee Meeeee(MMM) Meeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
M (MM8)8Me 88 [‌888‌]
M (M)-MM=MMMe 88 [‌888‌]
M Me 88 [‌888‌]
M 8-M8MM8M8 88 [‌888‌]
M 8-MeMM8M8 88 [‌888‌]
M 8-eeeeeee 88 [‌888‌]
M 88 [‌888‌]
(MM8)8 88 [‌888‌]
(MM8)8 88 [‌888‌]

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Meeeee 88 Meeeeeeee Meeeeeeeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee (Meeeeeeeeeeeeee)eeeeeee[‌888‌]

Meeeeeeee ee eeeeeeeeeee eeee eeeeee-8,8-eeeeeee ee eee eeeeeeee eeeeeeee(MM) eeeeeeee eeeee eee eeeeeeeeeeeee eeeeeeeeeeeee, eeeeeee eee eeeeeeeeeee, ee eeeeeeeee eeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeee(MM) Meeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee Meeeeeeeeee[‌888‌]

Meeeeeeee(MM) eeeeeeee ee e eeeeeeeeeeeeee eeeeeeee eee eeeeeeeee eeeeeeeeeeeeeeeeeee eeeeeee M,M-eeeeeee 888 eee eeeeee-8,8-eeeeeee ee eeee 8,8-eeeeeeeeeee 888 (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeee Meeeeeee ee Meeeeeeee(MM) Meeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M,M-Meeeee Meeee (%) Mee
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Meeee eeeee eeeeeeeeee, eeeeeee eeeeeee eeeee eeeeee eeee eeeeee eeeeeee (Meeeee 88).[‌888‌] Meeeee eeeeeee eeee ee 8,8-eeeeeeeeee eee 8,8-eeeeeeee eee eeeeeeeeee eeee eeeeeeee eee eeee eee eeeeeeeeeeeee 8,8-eeeeeeeeeee eeee eeeee eeeeeeeee eeeeeeee eeeee.

Meeeee 88 M Meeeeeeeee ee eee Meeeeeeeee ee Meeeeee eee Meeeee Meeeeee ee Meeeeeeee(MM) Meeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeeeeeeeeee ee M,M-eeeeeee 888 ee eeee 8,8-eeeeeeeeeee 888 eee ee eeeeeeee eeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeeeee(MM) eeeeeeee (Meeeee 88).[‌888‌] M,M-Meeeeee eeeeeee eeee eeeeee eeeeeeeee ee eeeeeee eee ee eeeeeeeee eeee eee eeeeeeeeeeeee 8,8-eeeeeeeeeee eeeeee 88 eeeeeee ee 88°M.

Meeeee 88 Meeeeeee(MM) Meeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meeee (%) Mee
M Me MMe MMe 88 [‌888‌]
M 8-Mee (MM8)8 88 [‌888‌]
M (M)-MM=MMMe (MM8)8 88 [‌888‌]
M (MM8)8Me (MM8)8 88 [‌888‌]
Me Me (MM8)8 88 [‌888‌]
(MM8)8 (MM8)8 88 [‌888‌]

Meeeeeeeee(M) eeeeeeee eeeeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeeeeee ee M,M-eeeeeee 888 ee 8,8-eeeeeeeeeee 888 ee eeeeeeeee eeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeee(M) Meeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌]

Meeeeee ee eeeeeeeeeee eee ee eeeeeeeeeee ee 8,8-eeeeeeeeeee ee e eeeeeeee eeeeeee. Mee eeeeeee, eeeeeeee eeeeee 888 ee eeeee eeeeeeeeeeeeeeeeee eeeee eeeeeeeeeeeeeee eeeeeeeeeeeeeee ee eeeee eeeeeeee 888, eee eeee eeeeeee eeeeeee eeee eeeeee-8,8-eeeeeee ee eeee eee eeeeeeeeeeeee 8,8-eeeeeeeeee 888 (Meeeee 88).[‌888‌] M eeeeeeeeeee ee e eeee eeeeee eeee, eeee ee eeeeeeeeee 8-eeeeeeeeeeeeeeee, eee e eeeeee Meeee eeee, eeee ee eeeeeeee eeeeeeeeeee eee eeee eeeeee eee eeeeeeeeee ee e eeeeeeeeee eeee e 8,8-eeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeee Meeeeeeeeee ee Meeeeee eeee 8,8-Meeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeeeeee Meeeeee:[‌88‌]

Me e eeee ee eeeeee-8,8-eeeeeee (8.888eM, 8.8eeee) eee MeMe8 (888ee, 8.8eeee) ee Me8M (8eM) ee ee eee eeeee eee M,M-eeeeee 888 (8.8eeee). Mee eeeeeee eee eeeeeee ee eee eeee eeeeeeeeeee eee 88eee eee eeeeeee eeee Me8M (88eM). Mee Me8M eeee eee eeeeee eeeeeeeeeeee eeee 88% MeMM, MM8Me eeee, eee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeee 8:88); eeeee: 8888%.

Meeeee 8-(8-Meeeeee-8-eeeeeeeeeeee-8-ee)-8-eeeeee-8,8-eeeeeeeeeee[8.8]eee-8-eee-8-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eee M,M-eeeeee 888 (8.88e, 8.88eeee) ee eeeeee-8,8-eeeeeee (88.8eM) eee eeeeeee eeee MM8MMe8 (8.8eM, 88eeee), eee eee eeeeeeee eee eeee ee ee eeeee ee eeeee eeeeeeeeee eee 88e. Mee eeeeeee eee eeee eeeeeee eeee MM8Me8 (88eM), eee eeeeee eeeeeeeee eeee eee. MeMMM8. Meeee eeeee eeeeeee eee 88eee, eee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeeeee (eeeeee eee Me8M/eeeeeee 8:8) eeeeeeee e eeeeeee eeee eeeeee eee; eeeee: 8.88e (88%).

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeee(MMM) Meeeeeeeeeeeeeeeeeeeeeeee:[‌888‌]

Me e eeee ee eee M,M-eeeeee eeeeeeee 888 (8eeee), ee eee eeeeee eeeeeeeee, eee eeeeee-8,8-eeeeeee (8.8eeee) ee MM8Me8 (88eM) eee eeeee eeeee Me(MMe)8 (8.88.88eeee) eeeee ee eeeee eeeeeeeeee. Mee eeeeeee eee eeeeeee ee ee eee eeeeeeeee ee MMM. MM8Me8 (88eM) eee M8M (88eM) eeee eeeee eee eee eeeeeee eeeee eee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (88eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee ee eeeeeee eeeeeee); eeeee: 8888%.

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeee(MMM) Meeeeeee:[‌888‌]

M eeeeeee ee M,M-eeeeee 888 (8eeee), eeeeee-8,8-eeeeeee (8.8eeee), eee eeeee MeMe8 (8eee%) ee MM8Me8 (8eM) eee eeeeeeee, eee eeee eeeeeeee eeee 88% MeMM (8eM). Mee eeeeeee eeeee eee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8888%.

8-Meeeee-8,8-eeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeee ee (eeeeeeeeeeeeeee)eeeeeee (8eeee) eee eeeeee-8,8-eeeeeee (8eeee) ee 8,8-eeeeeeeeeeeeee (88eM) eee eeeee eeeeeeee MeMe8 (8.88eeee). Mee eeeeeeee eee eeeeeee ee ee eee 88e. Meeeee eee eeeeee ee eeee eeeeee eeee Me eeeeeeeee eeeeeeeee ee e eeeee eeeeeee. Mee eeeeeeee eee eeee eeeeeeee eeee MeMMM8 (8.8e), eee eee eeeeeeeee eeeeeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee eeee eee eeeeeee; eeeee: 88%; ee 888°M/88Meee.

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeeeeee(MM) Meeeeeee:[‌888‌]

M eeeeeee ee M,M-eeeeee 888 (8eeee), eeeeee-8,8-eeeeeee (8.88.8eeee), eee MeMe8 (8.888.88eeee) ee eeeee MM8Me8 (88eM) eee eeeeeee ee ee. Mee eeeeeeee eee eeeeeeee eeee 88% MeMM (88eM), eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8×88eM), eee eeeee (Me8MM8). Meeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeeeee. Meeeeee eeeeeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8888%.

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeeeee(MM) Meeeeeee:[‌888‌]

M eeeeeee ee eee M,M-eeeeee 888 (8eeee), eeeeee-8,8-eeeeeee (8.8eeee), eee MMe8 (8.88.8eeee) ee eeeee MM8Me8 (88eM) eee eeeeeee 88°M eeeee eeeee (88eee eee M,M-eeeeeee eeeeeee eeee eeeeeeeee ee eeeee eeeeeee eee eeeeee eeeeeeee eeeee eee eeeee eeeeeee eeee eeeeeeee eeeeeee). Mee eeeeeeee eee eeeeeeee eeee 88% MeMM, eee eee eeeeeee eeeee eee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8×88eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee), eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee ee eeeeeeeeeeeeeeeee; eeeee: 8888%.

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeeeeeee(M) Meeeeeee:[‌888‌]

M eeeeeee ee M,M-eeeeee 888 (8eeee), eeeeee-8,8-eeeeeee (8.88.8eeee), eee MeMe8 (8.88eee%) ee MM8Me8 (88eM) eee eeeeeee ee ee eee eeeeeeee eeee 88% MeMM (88eM). Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8×88eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee) eeeeeeee ee eeeeeeeeeeee; eeeee: 8888%.

References