Asymmetric synthesis of 3, 3′-pyrrolidinyl-dispirooxindoles via a one-pot organocatalytic Mannich/deprotection/aza-Michael sequence. Issue 11 (4th January 2016)

• Record Type: Journal Article
• Authors: Zhao, Kun; Zhi, Ying; Li, Xinyi; Puttreddy, Rakesh; Rissanen, Kari; Enders, Dieter
• Is Part Of: Chemical communications. Volume 52:Issue 11(2016)
• Page Start: 2249
• Page End: 2252
• Publication Date: 2016-01-04
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c5cc10057g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A highly stereoselective synthesis of functionalized 3, 3′-pyrrolidinyl-dispirooxindole derivatives with three stereogenic centers, including two contiguous spiro-stereocenters, has been achieved through an organocatalytic Mannich/Boc-deprotection/aza-Michael sequence. Abstract : A highly stereoselective synthesis of functionalized 3, 3′-pyrrolidinyl-dispirooxindole derivatives with three stereogenic centers, including two contiguous spiro-stereocenters, has been achieved through an organocatalytic Mannich/Boc-deprotection/aza-Michael sequence. Employing the commercially available (DHQD)2 PHAL as the catalyst, the scalable reaction occurs with good yields and excellent stereoselectivities, providing a short entry into a series of 3, 3′-pyrrolidinyl-dispirooxindoles of potentially medical value.