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2.5.5.2 Asymmetric Hydrosilylation of Imines with Organocatalysts

DOI: 10.1055/sos-SD-202-00095

Xu, L.; Wu, X.; Xiao, J.Science of Synthesis: Stereoselective Synthesis, (20112285.

Asymmetric hydrosilylation of imines can be effected with chiral organocatalysts.[‌96‌‌100‌] Thus, the amides 63, 64, and 65 display high activity and enantioselectivity in the reduction of N-arylimines and N-alkylimines to the chiral amines 66 (Scheme 38).[‌97‌‌99‌] The amino acid derived diamide 67 is also a highly efficient and enantioselective Lewis base catalyst for reducing N-arylimines with trichlorosilane (Scheme 39).[‌100‌] The Lewis base presumably functions to increase the hydricity of the silane reagent.

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M8 M8 M8 Meeeeeee (eee%) Meeeeeeeee ee (%) Meeee (%) Mee
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8-M8MM8M8 Me Me 88 (88) MM8Me8, 8°M, 88e 88 88 [‌88‌]
8-M8MM8M8 Me Me 88 (88) MM8Me8, 8°M, 88e 88 88 [‌88‌]
8-MeM8M8 Me Me 88 (88) MM8Me8, 8°M, 88e 88 88 [‌88‌]
Me Me 8-Mee 88 (88) MM8Me8, 8°M, 88e 88 88 [‌88‌]
Me Me 8-MeM8M8 88 (88) MM8Me8, 8°M, 88e 88 88 [‌88‌]
Me Me Me 88 (88) MM8Me8, 8°M, 88e 88 88 [‌88‌]
8-MM8M8 Me Me 88 (88) MM8Me8, 88°M, 88e 88 88 [‌88‌]
8-MeM8M8 Me Me 88 (88) MM8Me8, 88°M, 88e 88 88 [‌88‌]
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Me Me Me 88 (88) eeeeeee, 8°M, 88e 88 88 [‌88‌]
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8-M8MM8M8 Me Me 88 (88) eeeeeee, 8°M, 88e 88 88 [‌88‌]
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8-eeeeeeee Me Me 88 (88) eeeeeee, 8°M, 88e 88 88 [‌88‌]
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8-M8MM8M8 Me MM8MM=MM8 88 (88) eeeeeee, 8°M, 88e 88 88 [‌88‌]
8-M8MM8M8 Me MM8MM=MM8 88 (88) eeeeeee, 8°M, 88e 88 88 [‌88‌]

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M8 M8 Me8 ee (%) Meeee (%) Mee
8-MeMM8M8 (MM8)8MM=MM8 8-MeMM8M8 88 88 [‌888‌]
Me (MM8)8Me 8-MeMM8M8 88 88 [‌888‌]
8-MMMMMMM8M8 8,8,8-(MeM)8M8M8(MM8)8 8-MeMM8M8 88 88 [‌888‌]
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8-MeM8M8 MM8Me 8-MeM8M8 88 88 [‌888‌]
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