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Transition-metal-mediated cascade reactions: The water-accelerated carboalumination-Claisen rearrangement-carbonyl addition reaction

Wipf, P and Waller, DL and Reeves, JT (2005) Transition-metal-mediated cascade reactions: The water-accelerated carboalumination-Claisen rearrangement-carbonyl addition reaction. Journal of Organic Chemistry, 70 (20). 8096 - 8102. ISSN 0022-3263

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Abstract

A three-step cascade reaction involving a water-accelerated catalytic carboalumination, a Claisen rearrangement, and a nucleophilic carbonyl addition converts terminal alkynes and allyl vinyl ethers into allylic alcohols containing up to three contiguous asymmetric carbon centers. Stoichiometric quantities of water as an additive increase the rate of the [3,3] sigmatropic rearrangement as well as the diastereoselectivity of the carbonyl addition process. Reaction products contain 1,6-diene functionalities that are readily cyclized to substituted cyclopentenes. An extension of this methodology to a sequence involving a [1,3] sigmatropic shift was feasible with a cyclopropylmethyl vinyl ether substrate. © 2005 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Waller, DL
Reeves, JT
Date: 20 September 2005
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 70
Number: 20
Page Range: 8096 - 8102
DOI or Unique Handle: 10.1021/jo051211v
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Acetylene--chemistry; Cinnamates--chemistry; Metals; Models, Molecular; Molecular Conformation; Organometallic Compounds--chemistry; Transition Elements; Vinyl Compounds--chemistry; X-Ray Diffraction
PubMed ID: 16277333
Date Deposited: 30 Jan 2014 17:02
Last Modified: 02 Feb 2019 15:57
URI: http://d-scholarship.pitt.edu/id/eprint/20405

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