One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization: Highly selective formation of three new bonds and two stereocenters in acyclic systems

Polina Smirnov; Jomon Mathew; Anne Nijs; Einat Katan; Miriam Karni; Carsten Bolm; Yitzhak Apeloig; Ilan Marek

doi:10.1002/anie.201306749

One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization: Highly selective formation of three new bonds and two stereocenters in acyclic systems

Polina Smirnov, Jomon Mathew, Anne Nijs, Einat Katan, Miriam Karni, Carsten Bolm, Yitzhak Apeloig, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

It's as easy as 1, 2, 3: In a one-pot sequence, two stereocenters and three new bonds were created with high selectivity through an asymmetric alkynylation of acyl silanes, a tandem Brook-type rearrangement and Zn-ene-allene cyclization, the addition of an electrophile, and finally oxidation (see scheme). The straightforward nature of the synthetic procedure contrasts strongly with the complexity of the densely functionalized products obtained.

Original language	English
Pages (from-to)	13717-13721
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	51
DOIs	https://doi.org/10.1002/anie.201306749
State	Published - 16 Dec 2013

Keywords

Brook rearrangement
acyl silanes
alkynylation
asymmetric synthesis
zinc

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

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10.1002/anie.201306749

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Smirnov, P., Mathew, J., Nijs, A., Katan, E., Karni, M., Bolm, C., Apeloig, Y., & Marek, I. (2013). One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization: Highly selective formation of three new bonds and two stereocenters in acyclic systems. Angewandte Chemie - International Edition, 52(51), 13717-13721. https://doi.org/10.1002/anie.201306749

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title = "One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization: Highly selective formation of three new bonds and two stereocenters in acyclic systems",

abstract = "It's as easy as 1, 2, 3: In a one-pot sequence, two stereocenters and three new bonds were created with high selectivity through an asymmetric alkynylation of acyl silanes, a tandem Brook-type rearrangement and Zn-ene-allene cyclization, the addition of an electrophile, and finally oxidation (see scheme). The straightforward nature of the synthetic procedure contrasts strongly with the complexity of the densely functionalized products obtained.",

keywords = "Brook rearrangement, acyl silanes, alkynylation, asymmetric synthesis, zinc",

author = "Polina Smirnov and Jomon Mathew and Anne Nijs and Einat Katan and Miriam Karni and Carsten Bolm and Yitzhak Apeloig and Ilan Marek",

year = "2013",

month = dec,

day = "16",

doi = "10.1002/anie.201306749",

language = "الإنجليزيّة",

volume = "52",

pages = "13717--13721",

journal = "Angewandte Chemie - International Edition",

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Smirnov, P, Mathew, J, Nijs, A, Katan, E, Karni, M, Bolm, C, Apeloig, Y & Marek, I 2013, 'One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization: Highly selective formation of three new bonds and two stereocenters in acyclic systems', Angewandte Chemie - International Edition, vol. 52, no. 51, pp. 13717-13721. https://doi.org/10.1002/anie.201306749

One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization: Highly selective formation of three new bonds and two stereocenters in acyclic systems. / Smirnov, Polina; Mathew, Jomon; Nijs, Anne et al.
In: Angewandte Chemie - International Edition, Vol. 52, No. 51, 16.12.2013, p. 13717-13721.

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

TY - JOUR

T1 - One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization

T2 - Highly selective formation of three new bonds and two stereocenters in acyclic systems

AU - Smirnov, Polina

AU - Mathew, Jomon

AU - Nijs, Anne

AU - Katan, Einat

AU - Karni, Miriam

AU - Bolm, Carsten

AU - Apeloig, Yitzhak

AU - Marek, Ilan

PY - 2013/12/16

Y1 - 2013/12/16

N2 - It's as easy as 1, 2, 3: In a one-pot sequence, two stereocenters and three new bonds were created with high selectivity through an asymmetric alkynylation of acyl silanes, a tandem Brook-type rearrangement and Zn-ene-allene cyclization, the addition of an electrophile, and finally oxidation (see scheme). The straightforward nature of the synthetic procedure contrasts strongly with the complexity of the densely functionalized products obtained.

AB - It's as easy as 1, 2, 3: In a one-pot sequence, two stereocenters and three new bonds were created with high selectivity through an asymmetric alkynylation of acyl silanes, a tandem Brook-type rearrangement and Zn-ene-allene cyclization, the addition of an electrophile, and finally oxidation (see scheme). The straightforward nature of the synthetic procedure contrasts strongly with the complexity of the densely functionalized products obtained.

KW - Brook rearrangement

KW - acyl silanes

KW - alkynylation

KW - asymmetric synthesis

KW - zinc

UR - http://www.scopus.com/inward/record.url?scp=84890488378&partnerID=8YFLogxK

U2 - 10.1002/anie.201306749

DO - 10.1002/anie.201306749

M3 - مقالة

SN - 1433-7851

VL - 52

SP - 13717

EP - 13721

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 51

ER -

One-pot zinc-promoted asymmetric alkynylation/brook-type rearrangement/ene-allene cyclization: Highly selective formation of three new bonds and two stereocenters in acyclic systems

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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