The unconventional reactivity of (Z)-enoate-attached propargylic alcohols in the presence of acids (nucleophilic and non-nucleophilic) was described. This study led to the discovery and development of a new strategy for the collective synthesis of the synthetically useful building blocks α-OMs-, α-OTs-, and α-Cl-enones, as well as 4,5-dioxonoates. The reaction proceeded under very mild conditions and showed a broad substrate scope. © 2017 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim

Beeraiah Baire

Department Of Chemistry

Prabhakararao Tharra

chemistry

Synthesis (chemical)

1,2-DIKETONES

ALPHA-HALOENONES

Building blockes

COLLECTIVE SYNTHESIS

Propargylic alcohols

Rearrangement

alcohols

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Chemistry - A European Journal

The Meyer–Schuster rearrangement of propargylic alcohols is a transformation in organic synthesis known for almost a century. The products of this reaction—α,β-enones and their α-functionalized units—are highly important functional groups for various synthetic transformations. Two modifications of this classical reaction, which involves interception of the intermediate allenol (or its equivalent) by either electrophiles or nucleophiles, have attracted the attention of synthetic organic chemists. This Focus Review provides a detailed description of the development of these two strategies. © 2018 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim

Asian Journal of Organic Chemistry

Intercepted Meyer–Schuster Rearrangements in Organic Synthesis

Unconventional Reactivity of (Z)-Enoate Propargylic Alcohols in the Presence of Acids

Brønsted acid promoted nucleophilation of propargylic alcohols during the Meyer-Schuster rearrangement (M-S) has been introduced. A novel concept of reverse polarization of the M-S intermediate allenyl cation has been realized by employing a cis-enoate assisted strategy. This idea is well demonstrated by the metal free synthesis of complex, highly functionalized cyclic as well as acyclic α-arylenones. The synthetic importance of the derived products was highlighted by the efficient conversion to biologically relevant molecules such as pyrazoles and 4,5-seco-abietane. © The Royal Society of Chemistry 2016.

Chemical Communications

The: Z -enoate assisted, Meyer-Schuster rearrangement cascade: Unconventional synthesis of α-arylenone esters

Synthetic Communications

Brønsted Acid–Catalyzed Meyer–Schuster Rearrangement for the Synthesis ofα,β-Unsaturated Carbonyl Compounds

Tetrahedron Letters

Iron-catalyzed indirect hydration of alkynes in presence of methanesulfonic acid

The Journal of Organic Chemistry

Enantioselective Syntheses of the Alkaloids cis-195A (Pumiliotoxin C) and trans-195A Based on Multiple Applications of Asymmetric Catalysis

Journal	Data powered by TypesetChemistry - A European Journal
Publisher	Data powered by TypesetWiley-VCH Verlag
ISSN	09476539
Open Access	No