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Title: Enantioselective Construction of Modular and Asymmetric Baskets
Abstract

The precise positioning of functional groups about the inner space of abiotic hosts is a challenging task and of interest for developing more effective receptors and catalysts akin to those found in nature. To address it, we herein report a synthetic methodology for preparing basket‐like cavitands comprised of three different aromatics as side arms with orthogonal esters at the rim for further functionalization. First, enantioenrichedA(borochloronorbornene),B(iodobromonorbornene), andC(boronorbornene) building blocks were obtained by stereoselective syntheses. Second, consecutiveA‐to‐Band thenAB‐to‐CSuzuki–Miyaura (SM) couplings were optimized to give enantioenrichedABCcavitand as the principal product. The robust synthetic protocol allowed us to prepare (a) an enantioenriched basket with three benzene sides and each holding either tBu, Et, or Me esters, (b) both enantiomers of a so‐called “spiral staircase” basket with benzene, naphthalene, and anthracene groups surrounding the inner space, and (c) a photo‐responsive basket bearing one anthracene and two benzene arms.

 
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PAR ID:
10308064
Author(s) / Creator(s):
 ;  ;  ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Angewandte Chemie International Edition
Volume:
60
Issue:
47
ISSN:
1433-7851
Page Range / eLocation ID:
p. 25075-25081
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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