Enantioselective addition of allyltin reagents to amino aldehydes catalyzed with bis(oxazolinyl)phenylrhodium(III) aqua complexes

Yukihiro Motoyama; Takatoshi Sakakura; Toshihide Takemoto; Kayoko Shimozono; Katsuyuki Aoki; Hisao Nishiyama

doi:10.3390/molecules16075387

Enantioselective addition of allyltin reagents to amino aldehydes catalyzed with bis(oxazolinyl)phenylrhodium(III) aqua complexes

Molecules. 2011 Jun 27;16(7):5387-401. doi: 10.3390/molecules16075387.

Authors

Yukihiro Motoyama¹, Takatoshi Sakakura, Toshihide Takemoto, Kayoko Shimozono, Katsuyuki Aoki, Hisao Nishiyama

Affiliation

¹ Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan. motoyama@cm.kyushu-u.ac.jp

Abstract

Bis(oxazolinyl)phenylrhodium(III) aqua complexes, (Phebox)RhX₂(H₂O) [X = Cl, Br], were found to be efficient Lewis acid catalysts for the enantioselective addition of allyl- and methallyltributyltin reagents to amino aldehydes. The reactions proceed smoothly in the presence of 5-10 mol % of (Phebox)RhX₂(H₂O) complex at ambient temperature to give the corresponding amino alcohols with modest to good enantioselectivity (up to 94% ee).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Catalysis
Molecular Structure
Rhodium / chemistry
Stereoisomerism

Substances

Aldehydes
Rhodium