Enantioselective Ru-Mediated Synthesis of (−)-Indolizidine 223AB

Douglass F. Taber; P. Bruce Deker; Lee J. Silverberg

doi:10.1021/jo00048a037

Enantioselective Ru-Mediated Synthesis of (−)-Indolizidine 223AB

Douglass F. Taber, P. Bruce Deker, Lee J. Silverberg

Penn State Schuylkill

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69 Scopus citations

Abstract

Triphenylphosphine/CCl₄-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (−)-indolizidine 223AB 4. Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine. Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAP·Ru*-mediated hydrogenation of the corresponding β-keto esters. A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80 °C and 50 psig of H₂.

Original language	English (US)
Pages (from-to)	5990-5994
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	57
Issue number	22
DOIs	https://doi.org/10.1021/jo00048a037
State	Published - Oct 1 1992

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Enantioselective Ru-Mediated Synthesis of (−)-Indolizidine 223AB",

abstract = "Triphenylphosphine/CCl4-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (−)-indolizidine 223AB 4. Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine. Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAP·Ru*-mediated hydrogenation of the corresponding β-keto esters. A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80 °C and 50 psig of H2.",

author = "Taber, {Douglass F.} and Deker, {P. Bruce} and Silverberg, {Lee J.}",

year = "1992",

month = oct,

day = "1",

doi = "10.1021/jo00048a037",

language = "English (US)",

volume = "57",

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journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Enantioselective Ru-Mediated Synthesis of (−)-Indolizidine 223AB

AU - Taber, Douglass F.

AU - Deker, P. Bruce

AU - Silverberg, Lee J.

PY - 1992/10/1

Y1 - 1992/10/1

N2 - Triphenylphosphine/CCl4-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (−)-indolizidine 223AB 4. Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine. Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAP·Ru*-mediated hydrogenation of the corresponding β-keto esters. A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80 °C and 50 psig of H2.

AB - Triphenylphosphine/CCl4-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (−)-indolizidine 223AB 4. Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine. Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAP·Ru*-mediated hydrogenation of the corresponding β-keto esters. A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80 °C and 50 psig of H2.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

Enantioselective Ru-Mediated Synthesis of (−)-Indolizidine 223AB

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