Organocatalytic Enantioselective Michael-Michael-Henry Reaction Cascade. An Entry to Highly Functionalized Hajos-Parrish-Type Ketones with Five to Six Contiguous Stereogenic Centers and Two Quaternary Carbons

Arun Raja; Bor-Cherng Hong; Ju-Hsiou Liao; Gene-Hsiang Lee

doi:10.1021/acs.orglett.6b00459

Organocatalytic Enantioselective Michael-Michael-Henry Reaction Cascade. An Entry to Highly Functionalized Hajos-Parrish-Type Ketones with Five to Six Contiguous Stereogenic Centers and Two Quaternary Carbons

Arun Raja
, Bor-Cherng Hong
, Ju-Hsiou Liao
, Gene-Hsiang Lee

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

28 Scopus citations

Abstract

An organocatalytic enantioselective reaction of 2-methylcyclopentane-1,3-dione, nitroalkene, and α,β-unsaturated aldehyde with the diphenylprolinol catalyst was developed to give the highly functionalized Hajos-Parrish-type ketones with five to six contiguous stereocenters and two quaternary carbon stereogenic centers with high diastereoselectivity and enantioselectivity. The structures of the adducts were unambiguously confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.

Original language	English
Pages (from-to)	1760-3
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.6b00459
State	Published - 15 Apr 2016
Externally published	Yes

Access to Document

10.1021/acs.orglett.6b00459

Fingerprint

Dive into the research topics of 'Organocatalytic Enantioselective Michael-Michael-Henry Reaction Cascade. An Entry to Highly Functionalized Hajos-Parrish-Type Ketones with Five to Six Contiguous Stereogenic Centers and Two Quaternary Carbons'. Together they form a unique fingerprint.

Cite this

@article{3d02305b8aca4f57a4d3072467d33af6,

title = "Organocatalytic Enantioselective Michael-Michael-Henry Reaction Cascade. An Entry to Highly Functionalized Hajos-Parrish-Type Ketones with Five to Six Contiguous Stereogenic Centers and Two Quaternary Carbons",

abstract = "An organocatalytic enantioselective reaction of 2-methylcyclopentane-1,3-dione, nitroalkene, and α,β-unsaturated aldehyde with the diphenylprolinol catalyst was developed to give the highly functionalized Hajos-Parrish-type ketones with five to six contiguous stereocenters and two quaternary carbon stereogenic centers with high diastereoselectivity and enantioselectivity. The structures of the adducts were unambiguously confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.",

author = "Arun Raja and Bor-Cherng Hong and Ju-Hsiou Liao and Gene-Hsiang Lee",

year = "2016",

month = apr,

day = "15",

doi = "10.1021/acs.orglett.6b00459",

language = "English",

volume = "18",

pages = "1760--3",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "8",

}

Organocatalytic Enantioselective Michael-Michael-Henry Reaction Cascade. An Entry to Highly Functionalized Hajos-Parrish-Type Ketones with Five to Six Contiguous Stereogenic Centers and Two Quaternary Carbons. / Raja, Arun; Hong, Bor-Cherng; Liao, Ju-Hsiou et al.
In: Organic Letters, Vol. 18, No. 8, 15.04.2016, p. 1760-3.

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

TY - JOUR

T1 - Organocatalytic Enantioselective Michael-Michael-Henry Reaction Cascade. An Entry to Highly Functionalized Hajos-Parrish-Type Ketones with Five to Six Contiguous Stereogenic Centers and Two Quaternary Carbons

AU - Raja, Arun

AU - Hong, Bor-Cherng

AU - Liao, Ju-Hsiou

AU - Lee, Gene-Hsiang

PY - 2016/4/15

Y1 - 2016/4/15

N2 - An organocatalytic enantioselective reaction of 2-methylcyclopentane-1,3-dione, nitroalkene, and α,β-unsaturated aldehyde with the diphenylprolinol catalyst was developed to give the highly functionalized Hajos-Parrish-type ketones with five to six contiguous stereocenters and two quaternary carbon stereogenic centers with high diastereoselectivity and enantioselectivity. The structures of the adducts were unambiguously confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.

AB - An organocatalytic enantioselective reaction of 2-methylcyclopentane-1,3-dione, nitroalkene, and α,β-unsaturated aldehyde with the diphenylprolinol catalyst was developed to give the highly functionalized Hajos-Parrish-type ketones with five to six contiguous stereocenters and two quaternary carbon stereogenic centers with high diastereoselectivity and enantioselectivity. The structures of the adducts were unambiguously confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.

U2 - 10.1021/acs.orglett.6b00459

DO - 10.1021/acs.orglett.6b00459

M3 - Article

C2 - 27080342

SN - 1523-7060

VL - 18

SP - 1760

EP - 1763

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -