syn-Selective Direct Catalytic Asymmetric Mannich-Type Reactions of Aromatic and Heteroaromatic Hydroxy Ketones Promoted by Y[N(SiMe3)2]3/Linked-BINOL Complexes

syn-Selective Direct Catalytic Asymmetric Mannich-Type Reactions of Aromatic and Heteroaromatic Hydroxy Ketones Promoted by Y[N(SiMe3)2]3/Linked-BINOL Complexes

Full details of syn-selective catalytic asymmetric direct Mannich-type reactions of aromatic and heteroaromatic hydroxy ketones promoted by Y[N(SiMe3)2]3/linked-BINOL complexes are described. From a screening of various rare-earth metals and linked-BINOL derivatives, a Y[N(SiMe3)2]3/TMS-linked-BINOL...

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Veröffentlicht in:Bulletin of the Chemical Society of Japan 2006-12, Vol.79 (12), p.1906-1912
Hauptverfasser: Matsunaga, Shigeki, Sugita, Mari, Yamagiwa, Noriyuki, Handa, Shinya, Yamaguchi, Akitake, Shibasaki, Masakatsu
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container_end_page 1912
container_issue 12
container_start_page 1906
container_title Bulletin of the Chemical Society of Japan
container_volume 79
creator Matsunaga, Shigeki
Sugita, Mari
Yamagiwa, Noriyuki
Handa, Shinya
Yamaguchi, Akitake
Shibasaki, Masakatsu
description Full details of syn-selective catalytic asymmetric direct Mannich-type reactions of aromatic and heteroaromatic hydroxy ketones promoted by Y[N(SiMe3)2]3/linked-BINOL complexes are described. From a screening of various rare-earth metals and linked-BINOL derivatives, a Y[N(SiMe3)2]3/TMS-linked-BINOL (1.7/1) complex was determined to be the most effective. Mannich-type reactions of aromatic and heteroaromatic hydroxy ketones with aryl and alkenyl N-diphenylphosphinoylimines, catalyzed by 0.1 molar amount of Y[N(SiMe3)2]3 and 0.059 molar amount of TMS-linked-BINOL, afforded syn-β-amino-α-hydroxy ketones in good yields (78–98%), high diastereoselectivity (syn/anti = 81/19–96/4), and high enantioselectivity (86–98% ee).
doi_str_mv 10.1246/bcsj.79.1906
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title syn-Selective Direct Catalytic Asymmetric Mannich-Type Reactions of Aromatic and Heteroaromatic Hydroxy Ketones Promoted by Y[N(SiMe3)2]3/Linked-BINOL Complexes
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