Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones : A Mechanistic Investigation

• The mechanism of a base-catalyzed one-pot reaction of 2-cyanobenzaldehyde and primary nitroalkanes, to produce 3-substituted isoindolinones, has been investigated. A route starting with a nitroaldol (Henry) reaction, followed by a subsequent cyclization and rearrangement, was supported by intermediate analogue synthesis and DFT calculations. Direct diastereoselective crystallization from the reaction mixture was also achieved and studied for a number of substrates. Furthermore, the 3-substituted isoindolinones are an interesting group of compounds, both present important natural products, as well as being precursors to other valuable building blocks.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

NATURVETENSKAP  -- Kemi -- Teoretisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)

Keyword

DYNAMIC COMBINATORIAL CHEMISTRY

DIELS-ALDER REACTIONS

ASYMMETRIC-SYNTHESIS

DRUG DISCOVERY

DERIVATIVES

RECEPTOR

ISOINDOLOBENZAZEPINE

2-CYANOBENZALDEHYDE

ISOINDOLIN-1-ONES

AUXILIARIES

Organic chemistry

Organisk kemi

Publication and Content Type

ref (subject category)

art (subject category)