Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction

Sherry R. Chemler; Samuel J. Danishefsky

doi:10.1021/ol0062547

Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction

Sherry R. Chemler
, Samuel J. Danishefsky

Chemistry

Memorial Sloan-Kettering Cancer Center
Columbia University

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

90 Scopus citations

Abstract

(equation presented) Transannular macrocyclizations via intramolecular B-alkyl Suzuki reactions are described. Regioselective terminal olefin hydroboration with 9-BBN followed by Pd(0)-catalyzed Suzuki reaction in the presence of a base such as TIOEt at high dilution generates macrocycles with a high degree of control over olefin geometry with isomerically pure E or Z vinyl iodide substrates. These reactions are complementary to ring closing metathesis (RCM) macrocyclizations and may prove superior in cases where control of olefin geometry is required.

Original language	English
Pages (from-to)	2695-2698
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	17
DOIs	https://doi.org/10.1021/ol0062547
State	Published - Aug 24 2000

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title = "Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction",

abstract = "(equation presented) Transannular macrocyclizations via intramolecular B-alkyl Suzuki reactions are described. Regioselective terminal olefin hydroboration with 9-BBN followed by Pd(0)-catalyzed Suzuki reaction in the presence of a base such as TIOEt at high dilution generates macrocycles with a high degree of control over olefin geometry with isomerically pure E or Z vinyl iodide substrates. These reactions are complementary to ring closing metathesis (RCM) macrocyclizations and may prove superior in cases where control of olefin geometry is required.",

author = "Chemler, \{Sherry R.\} and Danishefsky, \{Samuel J.\}",

year = "2000",

month = aug,

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doi = "10.1021/ol0062547",

language = "English",

volume = "2",

pages = "2695--2698",

journal = "Organic Letters",

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T1 - Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction

AU - Chemler, Sherry R.

AU - Danishefsky, Samuel J.

PY - 2000/8/24

Y1 - 2000/8/24

N2 - (equation presented) Transannular macrocyclizations via intramolecular B-alkyl Suzuki reactions are described. Regioselective terminal olefin hydroboration with 9-BBN followed by Pd(0)-catalyzed Suzuki reaction in the presence of a base such as TIOEt at high dilution generates macrocycles with a high degree of control over olefin geometry with isomerically pure E or Z vinyl iodide substrates. These reactions are complementary to ring closing metathesis (RCM) macrocyclizations and may prove superior in cases where control of olefin geometry is required.

AB - (equation presented) Transannular macrocyclizations via intramolecular B-alkyl Suzuki reactions are described. Regioselective terminal olefin hydroboration with 9-BBN followed by Pd(0)-catalyzed Suzuki reaction in the presence of a base such as TIOEt at high dilution generates macrocycles with a high degree of control over olefin geometry with isomerically pure E or Z vinyl iodide substrates. These reactions are complementary to ring closing metathesis (RCM) macrocyclizations and may prove superior in cases where control of olefin geometry is required.

UR - https://www.scopus.com/pages/publications/0034710497

U2 - 10.1021/ol0062547

DO - 10.1021/ol0062547

M3 - Article

C2 - 10990430

AN - SCOPUS:0034710497

SN - 1523-7060

VL - 2

SP - 2695

EP - 2698

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction

Abstract

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