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36.10.2.1.5 Method 5: Hydroboration of Allylic Substrates

DOI: 10.1055/sos-SD-036-00701

Bingham, M. J.; Greaney, M. F.Science of Synthesis, (2008361018.

The formal hydration of alkenes through hydroboration and sequential oxidation by basic peroxide is a fundamental functional-group interconversion in the chemistry of alcohols.[‌289‌,‌290‌] The reaction can be applied to a vast range of alkenes, including allylic nitrogen-, phosphorus-, oxygen-, sulfur-, selenium- or tellurium-containing compounds. As a result, it represents a reliable method for the synthesis of γheteroatom-substituted alcohols. Although the preparation of the requisite allyl substrates is generally beyond the scope of this section, the simplest method involves exploiting the nucleophilicity of the parent heteroatomic compound by conducting an allylation reaction with an allyl halide. The hydroboration/basic peroxide treatment then follows to produce the desired 1,3-difunctional compound with high regioselectivity; this sequence is illustrated for the carbamate starting material 89 (Scheme 45).[‌291‌]

Meeeee 88 Meeeeeeeee ee ee Meeee Meeeeeee ee Meeeeeeeeeeee/Meeeeeee Meeeeeeee[‌888‌]

Meeee 8 eeeee eeee eeeeeeee ee eee eeeeeeeeeeeee/eeeeeeee eeeeeeeee eee eeeeee-, eeeeee-, eeeeeeee-, eeeeeeee-, eee eeeeeeeeee-eeeeeeeeee eeeeeee eeeeeeeee (e.e., eeeeeeeeee ee 88 eeee 88).

Meeee 8 Meeeeeeeeeeee/Meeee Meeeeeee Meeeeeeee ee Meeee Meeeeeeeeee[‌88‌,‌888‌‌888‌]

Meeee Meeee Meeeeeeee Meeeeeeeee Meeeeee Meeee (%) Mee
8 8. 8-MMMM, MMM
8. M8M8, MeMM
88 [‌888‌]
8 8. 8-MMMM (8.8 eeeee), MMM, 8°M, 8.8e
8. M8M eeeeee, ee MeMM, 88% ee M8M8 (8.8 eeeee), 8°M, 8.8e
88 [‌888‌]
8 8. eeeeeeeeeeeeee (8 eeeee), [Me(eee)Me]8 (8eee%), Me8M (8eee%) MMM, ee, 88e
8. ee MeMM, 88% ee M8M8
88 [‌888‌]
8 8. 8-MMMM (8 eeeee), MeMe(MMe8)8 (8eee%), MMM, ee, 88e
8. ee MeMM, 88% ee M8M8 (eeeeee), 88°M, 8e
88 [‌88‌]
8 8. MMM (8.8 eeeee), MMM, 8°M ee ee, 8e
8. 8M ee MeMM, 8°M, 88% ee M8M8 (8 eeeee), 8e
88 [‌888‌]
8 8. 8-MMMM (8 eeeee), MMM, ee ee ­eeeeee, 8e
8. M8M eeeeee, 8 M ee MeMM, 88% ee M8M8 (eeeeee), 8°M ee ee, 88e
88 [‌888‌]
8 8. eeeeeeeeeeeeee (8 eeeee), MeMe(MMe8)8 (eee.), MMM, ee, 88e
8. ee MeMM, 88% ee M8M8
88 [‌888‌]
8 8. 8-MMMM (8 eeeee), MMM, ee, 88e
8. ee MeMM, 88% ee M8M8
88 [‌888‌]
8 8. MMM (8.88 eeeee), 8°M, 8e
8. M8M eeeeee, MeMM88M8M (8 eeeee), ee, 8e
88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

8-M-Meeeee-8,8-eeeeeee-8,8-M-eeeeeeeeeeeeee-M-eeeeeee-eeeeeee (88; Meeee 8, Meeee 8) [‌888‌]

MMM (8.888e, 8.88eeee) eee eeeee ee eee eeeeee 88 (888ee, 8.88eeee) ee eeeee MMM eeee 88eee eeeee eeeeeeeeeee e eeeeeeeeeee ee 8°M. Mee eeeeeee eee eeeeeee ee ee eee eeeeeee eee 8e. Mee eeeeeeeeeee eee eeee eeeeee ee 8°M eeeee 8M MeMM eee eeeee eeee eeeeee eeeee eee eeeeeee eee eeeee. M 88% eeee ee M8M8 ee M8M (8.88eM, 8.88eeee) eee eeeee, eee eee eeeeeee eee eeeeeee eee 8e eee eeee eeeeeeeee eeee MeMMe (8×88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eeeeeeeeeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee ee eeee e eeeeeeeee eeeeee; eeeee: 888ee (88%); [α]M88 +88.8 (e 8.88, MMMe8).

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