Enantioselective Synthesis of Functionalized Polycarbocycles via a Three-Component Organocascade Quadruple Reaction

Yun Pu Chang, Ramani Gurubrahamam, Kwunmin Chen

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

An efficient organocascade quadruple reaction was conducted to synthesize a functionalized spiropolycyclic scaffold in high chemical yields (43-80%) and excellent levels of stereoselectivity (up to >19:1 dr and 99% ee). The quadruple reaction proceeded smoothly between 1,3-indanedione and aromatic aldehydes with concomitant desymmetrization of prochiral 4-substituted cyclohexanones through the Knoevenagel/Michael/aldol/aldol reaction sequence catalyzed by a bifunctional thiourea catalyst. Two of the formed products were transformed into spirocyclic epoxides containing four contiguous quaternary centers.

Original languageEnglish
Pages (from-to)2908-2911
Number of pages4
JournalOrganic Letters
Volume17
Issue number12
DOIs
Publication statusPublished - 2015 Jun 19

Fingerprint

Cyclohexanones
Stereoselectivity
Thiourea
Epoxy Compounds
synthesis
Aldehydes
Scaffolds
epoxy compounds
thioureas
aldehydes
Catalysts
catalysts
products
3-hydroxybutanal
1,2-indanedione

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Enantioselective Synthesis of Functionalized Polycarbocycles via a Three-Component Organocascade Quadruple Reaction. / Chang, Yun Pu; Gurubrahamam, Ramani; Chen, Kwunmin.

In: Organic Letters, Vol. 17, No. 12, 19.06.2015, p. 2908-2911.

Research output: Contribution to journalArticle

@article{15c4b404259b4436bc683c7733d26e6d,
title = "Enantioselective Synthesis of Functionalized Polycarbocycles via a Three-Component Organocascade Quadruple Reaction",
abstract = "An efficient organocascade quadruple reaction was conducted to synthesize a functionalized spiropolycyclic scaffold in high chemical yields (43-80{\%}) and excellent levels of stereoselectivity (up to >19:1 dr and 99{\%} ee). The quadruple reaction proceeded smoothly between 1,3-indanedione and aromatic aldehydes with concomitant desymmetrization of prochiral 4-substituted cyclohexanones through the Knoevenagel/Michael/aldol/aldol reaction sequence catalyzed by a bifunctional thiourea catalyst. Two of the formed products were transformed into spirocyclic epoxides containing four contiguous quaternary centers.",
author = "Chang, {Yun Pu} and Ramani Gurubrahamam and Kwunmin Chen",
year = "2015",
month = "6",
day = "19",
doi = "10.1021/acs.orglett.5b01040",
language = "English",
volume = "17",
pages = "2908--2911",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "12",

}

TY - JOUR

T1 - Enantioselective Synthesis of Functionalized Polycarbocycles via a Three-Component Organocascade Quadruple Reaction

AU - Chang, Yun Pu

AU - Gurubrahamam, Ramani

AU - Chen, Kwunmin

PY - 2015/6/19

Y1 - 2015/6/19

N2 - An efficient organocascade quadruple reaction was conducted to synthesize a functionalized spiropolycyclic scaffold in high chemical yields (43-80%) and excellent levels of stereoselectivity (up to >19:1 dr and 99% ee). The quadruple reaction proceeded smoothly between 1,3-indanedione and aromatic aldehydes with concomitant desymmetrization of prochiral 4-substituted cyclohexanones through the Knoevenagel/Michael/aldol/aldol reaction sequence catalyzed by a bifunctional thiourea catalyst. Two of the formed products were transformed into spirocyclic epoxides containing four contiguous quaternary centers.

AB - An efficient organocascade quadruple reaction was conducted to synthesize a functionalized spiropolycyclic scaffold in high chemical yields (43-80%) and excellent levels of stereoselectivity (up to >19:1 dr and 99% ee). The quadruple reaction proceeded smoothly between 1,3-indanedione and aromatic aldehydes with concomitant desymmetrization of prochiral 4-substituted cyclohexanones through the Knoevenagel/Michael/aldol/aldol reaction sequence catalyzed by a bifunctional thiourea catalyst. Two of the formed products were transformed into spirocyclic epoxides containing four contiguous quaternary centers.

UR - http://www.scopus.com/inward/record.url?scp=84934891237&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84934891237&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b01040

DO - 10.1021/acs.orglett.5b01040

M3 - Article

AN - SCOPUS:84934891237

VL - 17

SP - 2908

EP - 2911

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 12

ER -