Stereodivergent Dual Catalytic α‐Allylation of Protected α‐Amino‐ and α‐Hydroxyacetaldehydes. (2nd October 2015)

• Record Type: Journal Article
• Authors: Sandmeier, Tobias; Krautwald, Simon; Zipfel, Hannes F.; Carreira, Erick M.
• Is Part Of: Angewandte Chemie. Volume 127:Number 48(2015)
• Page Start: 14571
• Page End: 14575
• Publication Date: 2015-10-02
• Subjects: Aldehyde -- Aminkatalyse -- Duale Katalyse -- Iridium -- Stereodivergenz; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201506933
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Fully stereodivergent dual‐catalytic α‐allylation of protected α‐amino‐ and α‐hydroxyacetaldehydes is achieved through iridium‐ and amine‐catalyzed substitution of racemic allylic alcohols with chiral enamines generated in situ. The operationally simple method furnishes useful aldehyde building blocks in good yields, more than 99 % ee, and with d.r. values greater than 20:1 in some cases. Additionally, the γ, δ‐unsaturated products can be further functionalized in a stereodivergent fashion with high selectivity and with preservation of stereochemical integrity at the Cα position.