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36.1.7.2.5 Variation 5: Catalytic, Enantioselective Additions of Organozinc Reagents

DOI: 10.1055/sos-SD-036-00193

Frost, C. G.; Le Nôtre, J.Science of Synthesis, (200836308.

The enantioselective addition of organozinc derivatives to carbonyl compounds has been a subject of great interest since the first example, described in 1984.[‌240‌] It was reported that the addition of diethylzinc to benzaldehyde in the presence of a catalytic amount of (S)-leucinol leads to the formation of (R)-1-phenylpropan-1-ol in 49% ee. Since this first discovery a plethora of methods have been developed and several reviews are available.[‌173‌,‌206‌‌210‌]

Me 8888, Meeeee eeeeeeeee eee eeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeee eeee eeee eeee eeeeeeeeeeeee, ee ee 88% ee, eeeee eeeeeee-eeeeeee eeeee eeeeeee 88 ee e eeeeeeeee eeeeee ee eeee eeeeeeee eeee ee 88 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeee ee Meeeeeeeeee Meeee e Meeeeee-Meeeeee Meeee Meeeeee Meeeeeee[‌888‌]

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Meeeee Meeeee (eee%) Meeeeee ee (%) Meeeeeee Mee
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8 88 [‌888‌]
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Meeeee eeeeeee eeeeeee eeeeeeee eeeee eee eeee eeeeeeeeeeee ee eee eeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeee eeeeeeeeeee ee eeeeeeee eeeeeeeee ee eeee eeeeeeee 88. M eeeeee ee eeeeeee eee eeeeeee eeee eeeeee eeeee eeee ee 88 (MMMMMM), eee eeee eeeeeeeeeeeeeeeeeeee eee ee eeeeeeee ee eee eeeeeeee eeeeeeee.[‌888‌] Mee eeeeee eeeeeeee eee eee ee e eeeeeeeee eeeeee ee eeeeee eeeeee ee eee eeeeeeee ee ee eeeeee ee e eeeeeeee eeeeeee, eeeeeee eeeeeeee(MM) eeeeeeeeeeee, eeeee eeeee ee eee eeeeeeeee ee e eeeeee eeeeeeee eeeee eee ee eee eeeeeeeeeee ee eeeeee eee eeeeeeeeeee ee eee eeeeeeee eeeeeeeee ee eee eeeeee ee eeeeeeee eeeeeeeee eee ee eee eeeeeeeee ee eee eeeeeeeeeeee ee eee eeeeee. Meeeeeee eeeeeeeee eeeeeee eee eeeeeeeee ee eeeeeee eee eee eeeeee eee eee ee eeeeeeee ee eeeeeee (Meeee 8).[‌888‌‌888‌]

Meeee 8 Meeeeee eee Meeee Meee Meeeeeee Meeeeeee ee Meeeeeeeeee Meeeeeee[‌888‌‌888‌]

Meeeee Meeeee (eee%) Meeeeee ee (%) Meeeeeee Mee
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Mee eeeeeeeee eeeee ee eeeeeee eee eee eeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeee eeeeeeeeeee ee eeeeeeee eeeeeeeee eeee eeee eeeeeeeeeee ee eeeeeeee eeee ee eeeeeeee ee eeeeeeeeee. Meee eeeeee eee eeeeeeeee ee eee eeeeeeeee eeee eeeeeeeee eeeeee eeeeeee eee eeeee eeeee eee eeeeeee eeeeeeeee eeeeeeeee. Meeeeeeeee-eeee eeeeeeeee eee eeee ee eeeeeeeee ee eeee eeeeee eee eeee eeeeeeeeeeeee. Me eeeeeeee ee eeeeeeeeeee eeeeee eeeeeee eee eeeeeeeeeeeeeeee eeeeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeee ee eeeeeeeee.[‌888‌]

Mee eeeeee eeee eeee eeeee eeeeeeeee eeeeee eeeeeee, eeee ee 88 (88eee% eeee, 8888% ee eeeeeeee eeee eeeee eeee)[‌888‌] ee 88 (88eee% eeee, 88% ee eeeeeeee)[‌888‌] ee eeeeeee ee eeee eeee eeee eee eee-eeeeeeeee eeeeeeeeeee. Meeeeeeeeeeee eee eeeeeeee ee eee eeee eeeee eeeee eeeeeee eeee (Meeeee 88).

Meeeee 88 Meeeeeeee Meeeee Meeeeee eee eee Meeeeeeeeeeeeeee Meeeeeee ee Meeeeeeeee Meeeeeee[‌888‌,‌888‌]

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Meeeee 88 Meeeeeee ee Meeeeeeeeee Meeeeeee Meeee Meee(MM) Meeeeeeeeeeeeeeeeeeeeeeee[‌888‌]

Mee ee eeee eeeeeeeeee ee eeeeeeeeeee eeeeeeeeeee eee eeee ee eeeeeeee eeeee eeeeeeeeeee eeeeeee ee eeeeeeeeee. Mee eeeeeeeeeeeeeeee eeeeeeee eeee eeeeeee eeee ee eeeeeeeeeeee ee eeee eeeeeeee.[‌888‌] Meeeeeeee-eeee eeeeeeeee eee ee eeee ee eeee eeeeeeee eee eeee, eeeee eeeeeeeeeeee ee eeeeeeeee, eee eeeeeeeeeeeee eeeeeeee eeeeeee 888 ee 88% ee (Meeeee 88).[‌888‌]

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Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeee-8-ee (88); Meeeeee Meeeeeeee:[‌888‌]

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8-Meeeeeeeeeee-8-ee (88, M8=MM8MM8Me; M8=Me); Meeeeee Meeeeeeee Meeee MMMMMM:[‌888‌]

Meee 88 (8.888e, 8.8eeee) eee eeeeee eeeee eeeee ee e eee 888-eM eeeee eeee e eeee eee. Me(MeMe)8 (8.88e, 8.8eeee) eee eeeeeee (88eM) eeee eeeee ee eeeeeee, eee, eeeee eeeeeeee ee ee eee 8e, eee eeeeeee eee eMeMM eeee eeeeeee (88°M/8×888 Meee). Mee eeeee eeeeeee eee eeeeeeee ee ee eeee eeeeeee (88eM) eee Me(MeMe)8 (8.8eM, 8.8e, 8.8eeee), eee eee eeee eee eeeeee ee 88°M (eeeeeeee). M 8M eeee ee Me8Me ee eeeeeee (8.8eM, 8.8eeee) eee eeee 8-eeeeeeeeeeeeee (8.88eM, 8.88e, 8.8eeee) eeee eeeee eeeeeeee. Meeee 88e ee 88°M (MMM eeeeeeee) eee eeeeeeee eee eeeeeeee eeee eee. ee MM8Me (88eM), eee Me8M (88eM) eee eeeee. Meeeeeee eee 88eee eee eeeeeeee ee eeeeeeeeee eeeeeee Meeeee, eeeeeee eeee eee. ee MeMe, eeeeee (Me8MM8), eee eeeeeee ee eee eeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee eeeeeee e eeeee eeeeee (eeeeee eee, eeeeee/Me8M 8:8), eee eee eeeeeeeee eeeeeee eee eeeeee ee e Meeeeeeee eeee (888°M/88Me) ee eeeee eee eeeeeeeeeeeee eeeeeee; eeeee: 8.8e (88%); ee 88°M.

Meeeeeeee Meeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M 88-eM eeeee eee eeeeeee eeee Me(MMe)8 (888ee, 8.888eeee, 8.8 eeeee) eee (+)-M-eeeeeeeeeeeeeee (88; 888ee, 8.888eeee, 8.8 eeeee) eee eeeeee eeee M8 eee 88eee. Meeeeee (8.8eM) eee Me8M (88ee, 8.888eeee, 8.8 eeeee) eeee eeeee, eee eee eeeeeeeee eeeeeee eee eeeeeee ee 88°M eee 8e eeeeee eee eeeeee (8.888eeee, 8.8 eeeee) eee eeeee ee eeeeeee ee eee eeeeeee. Meeee 88eee ee eeeeeeee, eee eeeeeeee eee eeeee ee eee eeeeeee ee eeeeeee, eee eee eeeeeee eee eeeeeee ee ee eee 888e. Mee eeeeeeee eee eeeeeeee ee eee eeeeeeee ee eee. ee MM8Me (8eM), eee eee eeeeeee eee eeeeee eeee e eeeeeeeeee eeeeee eeeeeeeeee Me8M (88eM). Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8×88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/Me8M 88:8) eeeeeeee eee eeeeeeeee eeeeeee; eeeee: 8888%.

References


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