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47.1.1.3.2.1.1 Variation 1: 1,2-Disubstituted Alkenes

DOI: 10.1055/sos-SD-047-00073

Markó, I. E.; Pospíšil, J.Science of Synthesis, (201047152.

The second-generation Julia alkenation reaction and especially its benzothiazol-2-yl sulfone (so-called S. Julia alkenation) and 1-phenyl-1H-tetrazol-5-yl sulfone (so-called JuliaKocienski alkenation) variations, have found wide application in the total synthesis of various natural products and their derivatives. The great advantage of this efficient connective method for alkene synthesis is that, in general, the reaction proceeds under mild conditions, and the stereoselectivity can be efficiently modulated by a proper choice of the solvent and the countercation (see Section 47.1.1.3.2).

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Meeeeeeeeeeee, ee eeee eeeee, eeeeeeee eeeeeee β-eeeeeee eeeeee eee ee eeeeeeeeeee eeeeeee ee eeeee eeee eeeeeeeee eee eeeee eee eeeeeee eeeeeee ee eeee eeeeee eee eeee eeee eeeeeeeeeee (Meeee 88, eeeeeee 8 eee 8). Meeeeee, eeeee eeeeee eee eeee ee eeeeeeeeeee eeeeeeee ee eeeeee-eeeeeeeeee Meeee eeeeeeeeee ee eeee ee eeeeeeeee eeeeee eee eeee eeeeee eeeeeeeeeee (eeeee 8).

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Meeee Meeeeeee Meeeeeee Meeeeeeeee Meeeeee Meeee (M/M) Meeee (%) Mee
8 MeMMMM, MMM/MMM, 88°M, eeee MMMM, MMM 88:88 88 [‌888‌]
8 MeMM8MM MMMMM, MMM, 88°M 88:8 88 [‌888‌]
8 M8M(MM8)8MM8MM M(MM8)8MMM MMMMM, MMM, 88°M ee ee M8MMM8MM=MM(MM8)8M 88:8 88e [‌888‌]
8 MeMMM8MM8MM 8-MeMM8M8MMM MeMMMM, MMM, 8°M 8-MeMM8M8MM=MMMMe 88:88 88 [‌888‌]
8 MMMMM, MMM, 88°M ee ee >88:8 88 [‌888‌]
8 Me(MM8)8MM8MM MMMMM, MMM, 88°M ee ee 88:88 88 [‌888‌]
8 MeMMMM, MMM/MMMM, 88°M ee ee 88:88 88 [‌888‌]
8 MMMMM, MMM, 88°M 88:88 88 [‌888‌]
8 MeMMMM, MMM/MMMM, 88°M >88:8 88 [‌888‌]

e MM=eeeeeeeeeeee-8-ee; MM=8-eeeeee-8M-eeeeeeee-8-ee.

e M8=MMMMM; M=MM8Me.

Meeeeeeeeeee Meeeeeeee

[(8M,8M,8M,8M,8M,8M,8M,8M,8M,8M)-8-{(M)-8-[(8M,8M)-8-Meeeeeeeeeeeeeeee]eeeee}eeeeeee(eeeeeeeeeee)-8-ee]eeeeeeee (Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee eee eeeeeeee (888ee, 8.888eeee, 8 eeeee) eee eee eeeeeee (888ee, 8.888eeee, 8.8 eeeee) ee MMM (88eM) ee 88°M eee eeeee eeeeeeee e 8M eeee ee MeMMMM ee MMM (8.8eM, 8.88eeee, 8.8 eeeee). Mee eeeeee eeee eee eeeeeee ee eeee eeeeeeeeeee eee 8e, eeee eeeeee ee 8°M, eee eeeeeee eee ee eeeeeeeeee 88eee. Mee eeeeeeee eee eeeeeeee eeee eee. ee MM8Me (8eM) eee eee eeeeeee eee eeeeeee eeee Me8M (88eM). Mee eeeeeee eeeee eee eeee eeeeee eeee 88% ee MMe (88eM), 8.8M MeMM (88eM), eee. ee MM8Me (88eM), eee eee. ee MeMe (88eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee 8M MMM eeeeeeee ee eee eeeee eeeeeee eeeeeeeee eeee e 8.88.8:8 eeeeeee ee M- eee M-eeeeeee eee eeee eeeeee. Mee eeeee eeeeeee eee eeeeeeee eeeeeeeee ee eeeeeeeeeeee eeeeeeeeee. Me e eeee ee eee eeeee eeeeee ee MMM (8eM) eee eeeee e 8M eeee ee MMMM ee MMM (8.88eM, 8.88eeee, 8.8 eeeee). Meeee 8e ee eeeeeeee ee ee, M8M (8eM) eee Me8M (88eM) eeee eeeee. Mee eeeeeee eeeee eee eeeeee eeee 88% ee MMe (88eM), eee. ee MeMMM8 (88eM), eee eee. ee MeMe (88eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeeeee eee eeeeeee eeeeeee ee e eeeeeeeee eee eeeeeeeeee ee e 8.88.8:8 eeeeeee ee eeeeee eeeeeee; eeeee: 888ee (88%).

(8M,8M)-8-Meeeeee-8-[(8M,8M,8M)-8-(eeeeeeeeeeeeee)-8-eeeee-8-eeeeeeeeee-8,8-eeee-8-ee]-8,8-eeeeeee-8M-eeeee (Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeeeeeeeeeeeeee eeeeeeee ee e eeeeeeee eeeee eeeeeeeeee eee ee eee eee eeee eeeeeeee.

Me e eeeee eeeeeee ee Me eeee, e eeee ee eee eeeeeeee (8.8e, 8.8eeee, 8.8 eeeee), eee eeeeeee (8.88e, 8.8eeee, 8.88 eeeee), eee MMMM (8.88eM) ee MMM (88eM) ee 88°M eee eeeeeee eeee e 8.8M eeee ee MeMMMM ee MMM (8.8eM, 8.8eeee, 8.88 eeeee). Meeee 8.8e, eee eeee eeeeeeeeeee eee eeeee ee 88°M. Mee eeeeeeee eee eeeeeeee eeee 88% ee MeMe (888eM), eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee. Meeee eeeeeeeeeeeeee eeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 888ee (88%); (M/M) >88:8.

References


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