Molecules 2011, 16(7), 5387-5401; doi:10.3390/molecules16075387
Article

Enantioselective Addition of Allyltin Reagents to Amino Aldehydes Catalyzed with Bis(oxazolinyl)phenylrhodium(III) Aqua Complexes

1,* email, 2, 2, 2, 2 and 3
Received: 30 May 2011; in revised form: 20 June 2011 / Accepted: 23 June 2011 / Published: 27 June 2011
(This article belongs to the Special Issue Catalytic Asymmetric Synthesis)
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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).
Keywords: allylation; amino aldehydes; Lewis acids; pincer ligands; rhodium
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Motoyama, Y.; Sakakura, T.; Takemoto, T.; Shimozono, K.; Aoki, K.; Nishiyama, H. Enantioselective Addition of Allyltin Reagents to Amino Aldehydes Catalyzed with Bis(oxazolinyl)phenylrhodium(III) Aqua Complexes. Molecules 2011, 16, 5387-5401.

AMA Style

Motoyama Y, Sakakura T, Takemoto T, Shimozono K, Aoki K, Nishiyama H. Enantioselective Addition of Allyltin Reagents to Amino Aldehydes Catalyzed with Bis(oxazolinyl)phenylrhodium(III) Aqua Complexes. Molecules. 2011; 16(7):5387-5401.

Chicago/Turabian Style

Motoyama, Yukihiro; Sakakura, Takatoshi; Takemoto, Toshihide; Shimozono, Kayoko; Aoki, Katsuyuki; Nishiyama, Hisao. 2011. "Enantioselective Addition of Allyltin Reagents to Amino Aldehydes Catalyzed with Bis(oxazolinyl)phenylrhodium(III) Aqua Complexes." Molecules 16, no. 7: 5387-5401.


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