Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation

Bruno D. Chapsal; Iwao Ojima

doi:10.1021/ol060181v

Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation

Bruno D. Chapsal
, Iwao Ojima

Chemistry

Stony Brook University

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

77 Scopus citations

Abstract

A highly efficient short total synthesis of (+)-γ-lycorane (>99% ee, 41% overall yield) was achieved by using the asymmetric allylic alkylation in the key step catalyzed by palladium complexes with novel chiral biphenol-based monodentate phosphoramidite ligands.

Original language	English
Pages (from-to)	1395-1398
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	7
DOIs	https://doi.org/10.1021/ol060181v
State	Published - Mar 30 2006

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title = "Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation",

abstract = "A highly efficient short total synthesis of (+)-γ-lycorane (>99\% ee, 41\% overall yield) was achieved by using the asymmetric allylic alkylation in the key step catalyzed by palladium complexes with novel chiral biphenol-based monodentate phosphoramidite ligands.",

author = "Chapsal, \{Bruno D.\} and Iwao Ojima",

year = "2006",

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doi = "10.1021/ol060181v",

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journal = "Organic Letters",

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T1 - Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation

AU - Chapsal, Bruno D.

AU - Ojima, Iwao

PY - 2006/3/30

Y1 - 2006/3/30

N2 - A highly efficient short total synthesis of (+)-γ-lycorane (>99% ee, 41% overall yield) was achieved by using the asymmetric allylic alkylation in the key step catalyzed by palladium complexes with novel chiral biphenol-based monodentate phosphoramidite ligands.

AB - A highly efficient short total synthesis of (+)-γ-lycorane (>99% ee, 41% overall yield) was achieved by using the asymmetric allylic alkylation in the key step catalyzed by palladium complexes with novel chiral biphenol-based monodentate phosphoramidite ligands.

UR - https://www.scopus.com/pages/publications/33645909124

U2 - 10.1021/ol060181v

DO - 10.1021/ol060181v

M3 - Article

C2 - 16562900

AN - SCOPUS:33645909124

SN - 1523-7060

VL - 8

SP - 1395

EP - 1398

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation

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