A samarium(II)-mediated, stereoselective cyclization for the synthesis of azaspirocycles

Giuditta Guazzelli; Lorna A. Duffy; David J. Procter

doi:10.1021/ol8017209

A samarium(II)-mediated, stereoselective cyclization for the synthesis of azaspirocycles

Giuditta Guazzelli, Lorna A. Duffy, David J. Procter

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

Abstract

(Chemical Equation Presented) Unsaturated keto-lactams undergo sequential conjugate reduction-aldol cyclization on treatment with SmI2 to give syn-spirocyclic pyrrolidinones and piperidinones containing vicinal, fully substituted stereocenters with complete diastereocontrol. The substituent on nitrogen and the lactam ring size have a marked impact on the efficiency of the spirocyclization. © 2008 American Chemical Society.

Original language	English
Pages (from-to)	4291-4294
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	19
DOIs	https://doi.org/10.1021/ol8017209
Publication status	Published - 2008

Keywords

ALPHA-PHOSPHONO LACTONES
PESTALOTIOPSIN-A
FUNCTIONALIZED
CYCLOBUTANOLS
STEREOCONTROLLED APPROACH
4-EXO-TRIG CYCLIZATION
UNSATURATED ALDEHYDES
DERIVATIVES
REDUCTION
IODIDE
CORE

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10.1021/ol8017209

CCDC 694541: Experimental Crystal Structure Determination
Guazzelli, G. (Contributor), Duffy, L. A. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2009
DOI: 10.5517/ccr9qk9, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccr9qk9&sid=DataCite
Dataset
CCDC 694542: Experimental Crystal Structure Determination
Guazzelli, G. (Contributor), Duffy, L. A. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2009
DOI: 10.5517/ccr9qlb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccr9qlb&sid=DataCite
Dataset

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@article{76f75a9e11dd49ab9bfd0140ee72e4b1,

title = "A samarium(II)-mediated, stereoselective cyclization for the synthesis of azaspirocycles",

abstract = "(Chemical Equation Presented) Unsaturated keto-lactams undergo sequential conjugate reduction-aldol cyclization on treatment with SmI2 to give syn-spirocyclic pyrrolidinones and piperidinones containing vicinal, fully substituted stereocenters with complete diastereocontrol. The substituent on nitrogen and the lactam ring size have a marked impact on the efficiency of the spirocyclization. {\textcopyright} 2008 American Chemical Society.",

keywords = "ALPHA-PHOSPHONO LACTONES, PESTALOTIOPSIN-A, FUNCTIONALIZED, CYCLOBUTANOLS, STEREOCONTROLLED APPROACH, 4-EXO-TRIG CYCLIZATION, UNSATURATED ALDEHYDES, DERIVATIVES, REDUCTION, IODIDE, CORE",

author = "Giuditta Guazzelli and Duffy, \{Lorna A.\} and Procter, \{David J.\}",

note = "Guazzelli, Giuditta Duffy, Lorna A. Procter, David J.",

year = "2008",

doi = "10.1021/ol8017209",

language = "English",

volume = "10",

pages = "4291--4294",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - A samarium(II)-mediated, stereoselective cyclization for the synthesis of azaspirocycles

AU - Guazzelli, Giuditta

AU - Duffy, Lorna A.

AU - Procter, David J.

N1 - Guazzelli, Giuditta Duffy, Lorna A. Procter, David J.

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) Unsaturated keto-lactams undergo sequential conjugate reduction-aldol cyclization on treatment with SmI2 to give syn-spirocyclic pyrrolidinones and piperidinones containing vicinal, fully substituted stereocenters with complete diastereocontrol. The substituent on nitrogen and the lactam ring size have a marked impact on the efficiency of the spirocyclization. © 2008 American Chemical Society.

AB - (Chemical Equation Presented) Unsaturated keto-lactams undergo sequential conjugate reduction-aldol cyclization on treatment with SmI2 to give syn-spirocyclic pyrrolidinones and piperidinones containing vicinal, fully substituted stereocenters with complete diastereocontrol. The substituent on nitrogen and the lactam ring size have a marked impact on the efficiency of the spirocyclization. © 2008 American Chemical Society.

KW - ALPHA-PHOSPHONO LACTONES

KW - PESTALOTIOPSIN-A

KW - FUNCTIONALIZED

KW - CYCLOBUTANOLS

KW - STEREOCONTROLLED APPROACH

KW - 4-EXO-TRIG CYCLIZATION

KW - UNSATURATED ALDEHYDES

KW - DERIVATIVES

KW - REDUCTION

KW - IODIDE

KW - CORE

U2 - 10.1021/ol8017209

DO - 10.1021/ol8017209

M3 - Article

SN - 1523-7052

VL - 10

SP - 4291

EP - 4294

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

A samarium(II)-mediated, stereoselective cyclization for the synthesis of azaspirocycles

Abstract

Keywords

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Datasets

CCDC 694541: Experimental Crystal Structure Determination

CCDC 694542: Experimental Crystal Structure Determination

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