Tetranuclear BINOL-titanium complex in selective direct aldol additions

The Journal of Organic Chemistry
Bernd SchetterR Mahrwald

Abstract

The extremely robust and water-stable tetranuclear complex Ti(4)(micro-BINOLato)(6)(micro(3)-OH)(4) (1) catalyzes the direct aldol addition with high degrees of regioselectivity at the sterically more encumbered alpha-side of unsymmetrical ketones. The formation of quaternary stereocenters is described. Oxygen-containing ene components can also be used as starting material in these reactions. When used with aliphatic aldehydes, acetals 18 or acetals of aldol adducts 20 were observed. As few as 0.2 mol % loadings with this catalyst 1 were enough to complete the reactions. Mechanistical aspects of the reactions are discussed.

References

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Citations

Aug 8, 2015·Accounts of Chemical Research·Scott A Ryken, Laurel L Schafer
Oct 13, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Rong-Hui WuLong-Guan Zhu
Jun 23, 2016·Chemical Communications : Chem Comm·Ning LiDominic S Wright
Oct 25, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Jayeeta BhattacharjeeTarun K Panda
Oct 7, 2014·Chemistry : a European Journal·Jesús M GarcíaClaudio Palomo
Dec 17, 2009·Chemistry, an Asian Journal·Steven D BullDiane E J E Robinson
Feb 6, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Jennifer A GardenCharlotte K Williams
Jan 29, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Suman DasTarun K Panda
Dec 23, 2009·Organic Letters·Abdul Majeed SeayadChristina L L Chai
Sep 28, 2018·Inorganic Chemistry·Jayeeta BhattacharjeeTarun K Panda
Jun 16, 2012·The Journal of Organic Chemistry·Yujiang MeiMatthew J Allen

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