Asymmetric Mannich‐Type Reaction of a Chiral N‐(tert‐Butylsulfinyl) Ketimine with Imines: Application to the Synthesis of Chiral 1,3‐Diamines

Abstract

Deprotonation of the chiral N-(tert-butylsulfinyl) ketimine 1 followed by trapping with imines 2 afforded the β-amino imines 3 as the Mannich-type products in high diastereoselectivities (99:1 dr). As versatile synthons chiral β-amino imines 3 could be transformed into enantiomeric β-amino ketone and chiral syn-or anti-1,3-diamines with high dia-

Synthesis of 1,3‐Diamines Through Rhodium‐Catalyzed CH Insertion

“…furnish selectively six-membered-ring heterocyclic products that are of interest as medicinal agents and as precursors to substituted 1,3-diamines, the latter transformation having been made possible under mild reaction conditions by using chemistries described herein. [7] The union of these methods represents a decided advance for CÀH amination technology.…”

Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones

“…Furthermore, the reaction was also applicable to alkyl β-keto acids, and comparable chemical yields and enantioselectivities were attainable ( Table 3 , entries 18–19). The absolute configurations of the products were assigned by comparing the optical rotation of 3a with the value reported in the literature [ 48 ] (see the Supporting Information File 1 for details).…”

Application of Chiral Sulfinamides into Formation and Reduction of Sulfinylketimines to Obtain Valuable α‐Chiral Primary Amines

“…After addition, they reduced successfully the product β‐hydroxyketimine, getting selectively syn product using catecholborane or anti product using lithium triethylborohydride (Scheme ). In 2006 Wang, Chen et al applied Ellman's addition conditions to N ‐tosylimines (instead of aldehydes) and obtained the expected products with perfect diastereoselectivities . They then applied the same reduction conditions and obtained as expected selectively syn products 2 using catecholborane and anti products 2 using lithium triethylborohydride, again with perfect diastereoselectivity (Scheme ).…”