Synthesis of “Garner” Aldehyde‐Derived Cyclopropylboronic Esters

Abstract

The ''Garner'' aldehyde has been used as a common intermediate for the preparation of the corresponding alkyne 7 and the alkenylboronic esters 12−16 (24−80%). Diastereoselective cyclopropanation afforded cyclopropylboronic esters 17−20 (60−84%, dr 22:78 to 92:8), the configurations of which were determined by chemical correlation (cyclopropanols 22), X-ray structural analysis (of 21a), and characteristic

Rhodium‐Catalyzed Arylation of Cyclopropenes Based on Asymmetric Direct Functionalization of Three‐Membered Carbocycles

“…To realize this goal, two possible scenarios could be envisaged:1 )the direct functionalization of an achiral cyclopropyl ring or 2) the direct functionalization of an achiral cyclopropenyl ring (Scheme 1b). [5,21] Having an interested in finding an alternative and step-economical solution to this problem, we wondered if we could develop ad irect highly diastereo-and enantioselective metal-catalyzed arylation of cyclopropenes. [18,19] Theo nly asymmetric direct functionalization of three-membered carbocycles,leading to arylated cyclopropanes from achiral cyclopropenes, consisted of ad iastereo-and enantioselective copper-catalyzed hydroboration, and subsequent palladium-catalyzed Suzuki-Miyaura cross-coupling reaction, reported by Tortosa [9] and others.…”

Arylcyclopropanes: Properties, Synthesis and Use in Medicinal Chemistry

“…91 The synthesis was achieved commencing with the hydroboration of 128, followed by formation of the boronic ester with either tartrate-derived diols (R,R)-112 or (S,S)-112, affording 130a and 130b. Alternatively, vinylboronic ester 131 was prepared using pinacol 129.…”

Suzuki–Miyaura Cross‐Coupling Reactions of Alkylboronic Acid Derivatives or Alkyltrifluoroborates with Aryl, Alkenyl or Alkyl Halides and Triflates

“…[55] Finally, in 2003 Pietruszka and co-workers reported the arylation of a functionalised cyclopropylboronic acid. [56] Scheme 30.…”