𝔖 Bobbio Scriptorium
✦   LIBER   ✦

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

✍ Scribed by Cui-Hua Zhao; Li Liu; Dong Wang; Yong-Jun Chen

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
201 KB
Volume
2006
Category
Article
ISSN
1434-193X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Deprotonation of the chiral N‐(tert‐butylsulfinyl) ketimine 1 followed by trapping with imines 2 afforded the β‐aminoimines 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 diastereomeric excess by hydrolysis or reduction, respectively. Moreover, the nucleophilic addition of organometallicreagents to chiral β‐amino imines 3 could provide 1,1,3‐trisubstituted 1,3‐diamines with high diastereoselectivities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

📜 SIMILAR VOLUMES

One-Pot Synthesis of Chiral Aziridines b
One-Pot Synthesis of Chiral Aziridines by a Domino Reaction by Using Desulfonylative Formation on the N-Tosyl Imine of Chloroacetaldehyde with an Asymmetric Mannich Reaction as a Key Step
✍ Prof. Dr. Yujiro Hayashi; Tatsuya Urushima; Daisuke Sakamoto; Kou Torii; Dr. Hay 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 English ⚖ 234 KB 👁 2 views

One-Pot Synthesis of Chiral Aziridines dure is simple, this method offers an efficient route for the preparation of chiral aziridine derivatives.

ChemInform Abstract: One-Pot Synthesis o
ChemInform Abstract: One-Pot Synthesis of Chiral Aziridines by a Domino Reaction by Using Desulfonylative Formation on the N-Tosyl Imine of Chloroacetaldehyde with an Asymmetric Mannich Reactions as a Key Step.
✍ Yujiro Hayashi; Tatsuya Urushima; Daisuke Sakamoto; Kou Torii; Hayato Ishikawa 📂 Article 📅 2012 🏛 John Wiley and Sons ⚖ 38 KB 👁 2 views

## Abstract The reaction of (I) with aldehydes (II) leads to a dia‐ and enantioselective formation of adducts (III).