Pre-Activation-Based Stereoselective Glycosylations: Pre-Activation-Based Stereoselective Glycosylations
- NSF-PAR ID:
- 10051119
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- European Journal of Organic Chemistry
- Volume:
- 2018
- Issue:
- 9
- ISSN:
- 1434-193X
- Page Range / eLocation ID:
- 1075 to 1096
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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Glycosyl phosphates are shown to be activated to stereospecific nucleophilic substitution reactions by precisely tailored bis-thiourea catalysts. Enhanced reactivity and scope is observed with phosphate relative to chloride leaving groups. Stronger binding (Km) to the H-bond donor and enhanced reactivity of the complex (kcat) enables efficient catalysis with broad functional group compatibility under mild, neutral conditions.