Enantioselective synthesis of planar-chiral 1, n -dioxa[ n ]paracyclophanes via catalytic asymmetric ortho -Lithiation

Kazumasa Kanda; Kohei Endo; Takanori Shibata

doi:10.1021/ol100444u

Enantioselective synthesis of planar-chiral 1, n -dioxa[ n ]paracyclophanes via catalytic asymmetric ortho -Lithiation

Kazumasa Kanda, Kohei Endo, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

Abstract

Figure presented Highly enantioselective ortho-lithiation and dilithiation of 1,n-dioxa[n]paracyclophanes were realized with the use of sec-butyllithium and a catalytic or stoichiometric amount of sparteine. Quenching with various electrophiles, such as iodine, iodomethane, and chlorodiphenylphosphine, afforded chiral mono- and disubstituted paracyclophanes with good to excellent ee.

Original language	English
Pages (from-to)	1980-1983
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	9
DOIs	https://doi.org/10.1021/ol100444u
Publication status	Published - 2010 May 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Figure presented Highly enantioselective ortho-lithiation and dilithiation of 1,n-dioxa[n]paracyclophanes were realized with the use of sec-butyllithium and a catalytic or stoichiometric amount of sparteine. Quenching with various electrophiles, such as iodine, iodomethane, and chlorodiphenylphosphine, afforded chiral mono- and disubstituted paracyclophanes with good to excellent ee.",

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T1 - Enantioselective synthesis of planar-chiral 1, n -dioxa[ n ]paracyclophanes via catalytic asymmetric ortho -Lithiation

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AU - Endo, Kohei

AU - Shibata, Takanori

PY - 2010/5/7

Y1 - 2010/5/7

N2 - Figure presented Highly enantioselective ortho-lithiation and dilithiation of 1,n-dioxa[n]paracyclophanes were realized with the use of sec-butyllithium and a catalytic or stoichiometric amount of sparteine. Quenching with various electrophiles, such as iodine, iodomethane, and chlorodiphenylphosphine, afforded chiral mono- and disubstituted paracyclophanes with good to excellent ee.

AB - Figure presented Highly enantioselective ortho-lithiation and dilithiation of 1,n-dioxa[n]paracyclophanes were realized with the use of sec-butyllithium and a catalytic or stoichiometric amount of sparteine. Quenching with various electrophiles, such as iodine, iodomethane, and chlorodiphenylphosphine, afforded chiral mono- and disubstituted paracyclophanes with good to excellent ee.

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JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Enantioselective synthesis of planar-chiral 1, n -dioxa[ n ]paracyclophanes via catalytic asymmetric ortho -Lithiation

Abstract

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