'Product Blog'
Glucosyl Thioureas – A New Type of Organocatalyst
A novel thiourea asymmetric organocatalysts that are bearing a glycosyl scaffold
Among the organocatalysts, thiourea-based organocatalysts are unique and popular due to their non-covalent catalysis. [1]. As we already discussed in one of our previous blogs, thioureas display bifunctional behavior determined by N–H donor groups with their unique dual hydrogen-bonding capacity and chiral moieties with high asymmetry inducing ability. These specific features make chiral thiourea an important catalytic tool in chiral synthesis.
The Strem Catalog in collaboration with Daicel, continues to introduce a novel series of thiourea organocatalysts that are bearing a glycosyl scaffold:
These bifunctional chiral thiourea organocatalysts consisting of a glycosyl group and a tertiary amino group are generated from readily available alpha-D-glucose [2]. Thiourea 07-0042 was proven to be an effective organocatalyst for the asymmetric aza-Henry reaction between N-Boc imines and nitromethane. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 99.8% ee) [2]. In addition, 07-0042 has shown up to 98% ee in asymmetric Michael addition of β-oxo phosphonate to nitro olefins [3]. 07-0043 is an effective organocatalyst for hydrogen-bond-directed enantioselective decarboxylative Mannich reaction of β-ketoacids with ketimines [4]. Thioureas with product numbers 07-0045 and 07-0046 also demonstrated high catalytic activity in highly enantioselective Michael addition reactions [5-7]. For more detailed product information please review corresponding technical note.
References:
- Org. Biomol. Chem. 2020, 18, 5513.
- Org. Lett. 2008, 10, 1707.
- Eur. J. Org. Chem. 2011, 3507.
- Angew. Chem. 2013, 125, 3961.
- RSC Adv. 2013, 3, 930.
- J. Org. Chem. 2010, 75, 1402.
- J. Org. Chem. 2012, 77, 6208.
