Publication

Pentadienyltitaniums as versatile intermediates: regio- and stereo-selectivities

Manfred Schlosser
2001
Journal Articles

Abstract

The adduct obtained upon consecutive treatment of 1,4-dienes with butyllithium in the presence of potassium tert-butoxide, chlorotri(isopropyloxy)titanium and a carbonyl compd. contains the a-hydroxyalkyl group invariably and exclusively linked to the 3-position of the former diene. When chlorotri(isopropyloxy)titanium is replaced by the Duthaler-Hafner reagent [(4R,5R)-chloro(cyclopentadienyl)(2,2-dimethyl-a,a,a',a'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato-O,Oa)titanium] the reaction does not only occur regioselectively but also with appreciably high enantioselectivity. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/a7d611bb-b8fd-4dca-b1be-95320a55e5d0

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Manfred Schlosser
2001
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/a7d611bb-b8fd-4dca-b1be-95320a55e5d0

About this result

Related concepts (20)

1,3-Dipolar cycloaddition

The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic application were established in the 1960s, primarily through the work of Rolf Huisgen. Hence, the reaction is sometimes referred to as the Huisgen cycloaddition (this term is often used to specifically describe the 1,3-dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-triazole).

Regioselectivity

In chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will be added. A specific example is a halohydrin formation reaction with 2-propenylbenzene: Because of the preference for the formation of one product over another, the reaction is selective.

Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.