Organocatalytic asymmetric synthesis of chiral pyrrolizines by cascade conjugate addition-aldol reactions

Ju Yeon Bae; Hyo Jun Lee; Seok Ho Youn; Su Hyun Kwon; Chang Woo Cho

doi:10.1021/ol101811c

Organocatalytic asymmetric synthesis of chiral pyrrolizines by cascade conjugate addition-aldol reactions

Ju Yeon Bae, Hyo Jun Lee, Seok Ho Youn, Su Hyun Kwon, Chang Woo Cho

Kyungpook National University

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

47 Scopus citations

Abstract

Figure Presented. As the first N-centered heteroaromatic nucleophile for organocatalytic cascade reactions, pyrroles underwent the enantio- and diastereoselective organocatalytic cascade conjugate addition-aldol reactions of α,β-unsaturated aldehydes that afford the highly functionalized chiral pyrrolizines bearing three consecutive stereocenters in good yields, high enantioselectivities (90-98% ee), and excellent diastereoselectivities (>20:1 dr in all cases).

Original language	English
Pages (from-to)	4352-4355
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	19
DOIs	https://doi.org/10.1021/ol101811c
State	Published - 1 Oct 2010

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title = "Organocatalytic asymmetric synthesis of chiral pyrrolizines by cascade conjugate addition-aldol reactions",

abstract = "Figure Presented. As the first N-centered heteroaromatic nucleophile for organocatalytic cascade reactions, pyrroles underwent the enantio- and diastereoselective organocatalytic cascade conjugate addition-aldol reactions of α,β-unsaturated aldehydes that afford the highly functionalized chiral pyrrolizines bearing three consecutive stereocenters in good yields, high enantioselectivities (90-98\% ee), and excellent diastereoselectivities (>20:1 dr in all cases).",

author = "Bae, \{Ju Yeon\} and Lee, \{Hyo Jun\} and Youn, \{Seok Ho\} and Kwon, \{Su Hyun\} and Cho, \{Chang Woo\}",

year = "2010",

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doi = "10.1021/ol101811c",

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journal = "Organic Letters",

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T1 - Organocatalytic asymmetric synthesis of chiral pyrrolizines by cascade conjugate addition-aldol reactions

AU - Bae, Ju Yeon

AU - Lee, Hyo Jun

AU - Youn, Seok Ho

AU - Kwon, Su Hyun

AU - Cho, Chang Woo

PY - 2010/10/1

Y1 - 2010/10/1

N2 - Figure Presented. As the first N-centered heteroaromatic nucleophile for organocatalytic cascade reactions, pyrroles underwent the enantio- and diastereoselective organocatalytic cascade conjugate addition-aldol reactions of α,β-unsaturated aldehydes that afford the highly functionalized chiral pyrrolizines bearing three consecutive stereocenters in good yields, high enantioselectivities (90-98% ee), and excellent diastereoselectivities (>20:1 dr in all cases).

AB - Figure Presented. As the first N-centered heteroaromatic nucleophile for organocatalytic cascade reactions, pyrroles underwent the enantio- and diastereoselective organocatalytic cascade conjugate addition-aldol reactions of α,β-unsaturated aldehydes that afford the highly functionalized chiral pyrrolizines bearing three consecutive stereocenters in good yields, high enantioselectivities (90-98% ee), and excellent diastereoselectivities (>20:1 dr in all cases).

UR - http://www.scopus.com/inward/record.url?scp=77957164101&partnerID=8YFLogxK

U2 - 10.1021/ol101811c

DO - 10.1021/ol101811c

M3 - Article

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AN - SCOPUS:77957164101

SN - 1523-7060

VL - 12

SP - 4352

EP - 4355

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Organocatalytic asymmetric synthesis of chiral pyrrolizines by cascade conjugate addition-aldol reactions

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