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  • Aliphatic imines in titanium-mediated reductive cross-coupling: unique reactivity of Ti(O-i-Pr)4/n-BuLi.

Aliphatic imines in titanium-mediated reductive cross-coupling: unique reactivity of Ti(O-i-Pr)4/n-BuLi.

Organic letters (2009-10-09)
Michael A Tarselli, Glenn C Micalizio
ABSTRACT

A procedure for the coupling of aliphatic imines with allylic and allenic alkoxides is described. The success of these studies was enabled by a unique reactivity profile of Ti(IV) isopropoxide/n-BuLi compared to well-known Ti(IV) isopropoxide/RMgX systems.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
n-Butyllithium solution, 2.5 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 11.0 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 2.7 M in heptane
Sigma-Aldrich
n-Butyllithium solution, 2.0 M in cyclohexane
Sigma-Aldrich
n-Butyllithium solution, 1.6 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 1.4 M in toluene