Atom Economic Asymmetric Aldol and Related Reactions

Applications

• Fine chemicals - synthesis of chiral intermediates
• Pharmaceutical synthesis - natural products and small molecules
• Agrichemical synthesis

Advantages

• Versatile -
• Reaction works with a variety of ketones, nitroalkyls, carbonyls, and imines
• Catalyst can be used for aldol, nitroaldol, and other reactions
• Inexpensive -
• High atom economy of reaction
• Low cost of chiral ligand
• Catalyst utilizes low cost metal
• Easy - chiral ligand readily available
• Non-toxic metal in catalyst

Publications

• B.M. Trost and H. Ito "A Direct Catalytic Enantioselective Aldol Reaction via a Novel Catalyst Design," J Am Chem Soc 2000, 22, 12003-12004.
• Trost BM, Ito H, Silcoff Er. "Asymmetric aldol reaction via a dinuclear zinc catalyst: alpha-hydroxyketones as donors" J Am Chem Soc. 2001 Apr 11:123(14):3367-8.
• Trost BM, Silcoff ER, Ito H. "Direct asymmetric aldol reactions of acetone using bimetallic zinc catalysts" Org Lett. 2001 Aug 9;3(16):2497-500.
• Trost BM, Yeh VS. "A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction." Angew Chem Int Ed Engl. 2002 Mar 1;41(5):861-3.
• Trost BM, Yeh VS, Ito H, Bremeyer N. "Effect of ligand structure on the zinc-catalyzed Henry reaction: Asymmetric syntheses of (-)-denopamine and (-)-arbutamine." Org Lett. 2002 Aug 8:4(16):2621-3.
• Trost BM, Yeh VS, "Stereocontrolled synthesis of (+)-boronolide" Org Lett. 2002 Oct 3:4(20):3213-6.
• Trost BM, Terrell LR. "A direct catalytic asymmetric mannich-type reaction to syn-amino alcohols." J Am Chem Soc. 2003 Jan 15;125(2):338-9.
• Trost BM, Fettes A, Shireman BT. "Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction." J Am Chem Soc. 2004 Mar 10;126(9):2660-1.
• Trost BM, Frederiksen MU, Papillon JP, Harrington PE, Shin S, Shireman BT. "Dinuclear asymmetric Zn aldol additions: formal asymmetric synthesis of fostriecin." J Am Chem Soc. 2005 Mar 23:127(11):3666-7.

Lab Web Site

Web Page of B.M. Trost Group

Patents

• Published Application: WO200241984
• Published Application: 20040019239