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Methylsulfonyl-Based Sulfamide-Amine Alcohol as a Ligand for Enantioselective Alkynylation of Aldehydes

✍ Scribed by Wei JIN; Yongbo HUANG; Boshun WAN

Publisher
Elsevier Science
Year
2010
Weight
296 KB
Volume
31
Category
Article
ISSN
1872-2067

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✦ Synopsis

Chiral methylsulfonyl-based sulfamide-amine alcohol (SAA) ligands were synthesized from commercially available starting materials in two simple steps. Methylsulfonyl-based SAA ligands catalyzed the asymmetric alkynylation of various aldehydes using alkynylzinc to provide chiral propargyl alcohols with moderate to good enantioselectivity up to 83% ee.

πŸ“œ SIMILAR VOLUMES

l-Proline-derived tertiary amino alcohol
l-Proline-derived tertiary amino alcohol as a new chiral ligand for enantioselective alkynylation of aldehydes
✍ Zhou Xu; Nan Wu; Zhenhua Ding; Ting Wang; Jincheng Mao; Yawen Zhang πŸ“‚ Article πŸ“… 2009 πŸ› Elsevier Science 🌐 French βš– 330 KB

The easily prepared chiral tertiary amino alcohol 1a was found to catalyze the reaction of alkynylzinc reagents with various aldehydes to generate chiral propargylic alcohols with moderate-to-good enantioselectivities. The mechanism of the reaction is also discussed in this Letter. A novel theoretic