S_N2′ Boron‐Mediated Mitsunobu Reactions – A New One‐Pot Three‐Component Synthesis of Substituted Enamides and Enol Benzoates

Abstract

The conversion of (3-hydroxy-1-propen-1-yl)boronates to substituted enamides and enol benzoates is readily achieved in a one-pot procedure consisting of a regiocontrolled Mitsunobu reaction with convenient nucleophiles, followed by allylboration of aldehydes.

Modelling Binuclear Metallobiosites: Insights from Pyrazole‐Supported Biomimetic and Bioinspired Complexes

“…More recently, another elegant diastereoselective method was also reported based on a copper‐catalyzed addition of bis(pinacolato)diboron to N ‐ tert ‐butanesulfinyl aldimines 4b. Other approaches are more limited in terms of generality by the nature of the starting products, such as borylation of organometallic compounds,4c S N 2′ reactions,4d,e electrophilic amination4f or [3,3]‐sigmatropic rearrangements 4g…”

Antibacterial Agents and Cystic Fibrosis: Synthesis and Antimicrobial Evaluation of a Series of N‐Thiomethylazetidinones

“…The Z / E ratio and the cis/trans ratio of the bicyclic compound are identical to those obtained with the corresponding carboxylic amino ester under the same catalytic conditions. Similarly, bicyclic boroproline derivative 13 was synthesised from borated 1,6‐enyne 12 ,19 with a good yield as a major diastereomer (95/5). Besides a potential interest in medicinal chemistry, these compounds should be also of great significance for the synthesis of various 2‐substituted constrained bicyclic proline and pipecolic acid analogues via Suzuki–Miyaura couplings 21…”

Palladium‐Catalyzed Diastereoselective Synthesis of (Z)‐Conjugated Enynyl Homoallylic Alcohols

“…To address the racemization process, we envisioned that a competing reaction involving palladium‐catalyzed alkene isomerization of ( R )‐ 2 a followed by allylboration of benzaldehyde may also occur [27a] if the palladium‐catalyzed coupling of homoaldol equivalent 5 with 3 a is feasible (Scheme 3a). This is because homoaldol equivalent 5 is known to be produced in its racemic form [27b] .…”