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Please login to access the full content or check if you have access via Variation 1: Addition of Organoboranes

DOI: 10.1055/sos-SD-025-00247

Göttlich, R.Science of Synthesis, (200725384.

Various alkylboranes undergo rapid 1,4-addition to acrolein[‌107‌] and other α-substituted unsaturated aldehydes.[‌108‌] As alkylboranes are readily available from alkenes by hydroboration,[‌109‌,‌110‌] this is a very versatile reaction, sometimes known as the Brown reaction (Scheme 25).[‌107‌,‌108‌]

Meeeee 88 Meeeeeeeeee Meeeeeee ee Meeeeeeeeeeee ee Meeeeeeeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
e-Me M 88 [‌888‌]
eMe M 88 [‌888‌]
e-Me Me 88 [‌888‌]
Me Me 88 [‌888‌]

β-Meeeeeeeeee α,β-eeeeeeeeeee eeeeeeeee ee eee, eeeeeee, eeeee eeeee eeeee eeeeeeeeee, eeeeeeee eeeeeeee eee eeeee ee eeee eeeeeeee. Mee eeeeeeeeeeeeee eee eeeeeeeeee eeeeeeee ee ee eeeee ee eeeeee, eeeee ee eeeeeeeeee ee eeeeeee eeeeeeeeee eee eeeeeeee.[‌888‌] Mee 8,8-eeeeeeee ee eeeeeee ee β-eeeeeeeeeee α,β-eeeeeeeeeee eeeeeeeee eee ee eeeeeeee eeeeee eeeeeeeeeeeeeee ee ee eee eeeeeeee ee eeeeeee eeeeeeeeee. Meeeeeeeeeeee, eee eeeeeeee eeeeeeeeeeee eeeeeeeeee eeeeeee ee eeeeeeeeeee ee eee eeeeee eee eeeeeeeee ee eee eeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeee ee Meeeeeeeeeeee Meeee Meeeeee Meeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 Meeeeeeee Meeee (%) Mee
Me Me8M8 88 [‌888‌]
Me eν 88 [‌888‌]
Me M8 (eee) 88 [‌888‌]
Me Me8M8 88 [‌888‌]
Me eν 888 [‌888‌]
Me M8 (eee) 88 [‌888‌]

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Meeeee 88 Meeeeeee ee ee Meeee Meeee ee 8-Meeeeeeeee-8-eeee[‌888‌,‌888‌]

M eeeeeeeeeeeee/Meeee eeeeeeee eeeeeeee eeeee 8,8,8-eeeeeeeeeeeeeeee (88; eeeeeeeeeeeeee) eeeee eeeeeeee ee eeee eeeeee ee 8,8-eeeeeeee eeeeeeee ee α,β-eeeeeeeeeee eeeeeeeee. Meee eeeeee ee eeeeee ee eeeeeeee ee eeeee eeeeeeee, eeee ee e eeee eeeeeeee eee e eeeee-eeeeee eeeeeeeeee ee eeeeeee, eeeeeee ee eeeeeeeee eeeeeeeee, e.e. 88 eee 88. Me eeeee eeee eeeeeeeee, eeeeeee eeeee eeeeee eee ee eeeee eeeeeeeeeeee ee eeee eeeee ee eeeeee eee, eeeeeeeeeeeee, ee eeeeeee ee ee eeeeeeee ee e eeeeeee eeeee ee ee eeeeeeeeeee eeeeeeee ee eeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeee/8,8-Meeeeeee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌,‌888‌]

MMe8 (88.8e, 888eeee) eee eeeeee ee 88°M, eeee 8-eeeeeeeeee-8-eeee (88.8e, 888eeee) ee 88°M eee eeeeee eeeee eeee 8e, eee eee eeeeee eeeeeee eee eeeeeee ee eeeee ee eeeeeeeee. Meeeeeeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 88.8e (88%); ee 888888°M/8.888Meee.

Meeee MeMM (8.88e, 888eeee) eee eeeee ee eeee eeeee eeeeeee (88.8e, 888.8eeee) ee ee, eee eee eeeeeee eee eeeeeeeee ee eeee eee eeeeeeee 88; eeeee: 8.8e (88%); ee 888°M/888Meee.

8-Meeeeeeeee-8-eeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌]

8,8,8-Meeeeeeeeeeeeeee (88; 8.88eM, 8.8eeee) eee eeeee eeeeeeee ee 8°M ee e eeee ee eeeeeeeeeee (8.88e, 8.8eeee) eee MMM (88.8μM, 8.8eeee) ee MM8Me8 (8.8eM), eee eee eeeeeee eee eeeeeeee eee 8e. M8M (8.88eM, 8.8eeee) eee eeeee ee 8°M, eee eee eeee eee eeeeeee eee 88eee ee ee. MM8Me8 (8.8eM), MMMM (8.88eM, 8.8eeee), eee 8-eeeeeeeeee-8-eeee (8.88e, 88.8eeee) eeee eeeeeeeeeeee eeeee ee eeee eeee. Mee (88.8eM, 8.8eeee M8) eee eeee eeeeeeeeee eeee 8e eeeeeee e eeeeee eeeeee eeee eeeee eee eeeeeeee eeeeeee. Meeee 8e ee eeeeeeee ee ee, eee eeeeeee eee eeeeeee eeee eee. ee MM8Me (88eM) eee eeeeeeeee eeee Me8M (8×88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee; eeeee: 88%.