Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: Synthesis of highly substituted chiral spirodihydrocoumarins

Dhevalapally B. Ramachary; R. Madhavachary; M. Shiva Prasad

doi:10.1039/c2ob07122c

Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: Synthesis of highly substituted chiral spirodihydrocoumarins

Dhevalapally B. Ramachary^*, R. Madhavachary, M. Shiva Prasad

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

45 Citations (Scopus)

Abstract

A general approach to asymmetric synthesis of highly substituted spirodihydrocoumarins with a quaternary stereocenter was achieved through neighboring ortho-hydroxyl group induced sequential Michael-lactonization reactions on 2-(2-nitrovinyl)phenols with alkyl cyclopentanone-2-carboxylates in the presence of a catalytic amount of quinine-NH-thiourea followed by p-TSA.

Original language	English
Pages (from-to)	5825-5829
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	30
DOIs	https://doi.org/10.1039/c2ob07122c
Publication status	Published - 14 Aug 2012

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title = "Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: Synthesis of highly substituted chiral spirodihydrocoumarins",

abstract = "A general approach to asymmetric synthesis of highly substituted spirodihydrocoumarins with a quaternary stereocenter was achieved through neighboring ortho-hydroxyl group induced sequential Michael-lactonization reactions on 2-(2-nitrovinyl)phenols with alkyl cyclopentanone-2-carboxylates in the presence of a catalytic amount of quinine-NH-thiourea followed by p-TSA.",

author = "Ramachary, {Dhevalapally B.} and R. Madhavachary and Prasad, {M. Shiva}",

year = "2012",

month = aug,

day = "14",

doi = "10.1039/c2ob07122c",

language = "English",

volume = "10",

pages = "5825--5829",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "30",

}

Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: Synthesis of highly substituted chiral spirodihydrocoumarins. / Ramachary, Dhevalapally B.; Madhavachary, R.; Prasad, M. Shiva.
In: Organic and Biomolecular Chemistry, Vol. 10, No. 30, 14.08.2012, p. 5825-5829.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions

T2 - Synthesis of highly substituted chiral spirodihydrocoumarins

AU - Ramachary, Dhevalapally B.

AU - Madhavachary, R.

AU - Prasad, M. Shiva

PY - 2012/8/14

Y1 - 2012/8/14

N2 - A general approach to asymmetric synthesis of highly substituted spirodihydrocoumarins with a quaternary stereocenter was achieved through neighboring ortho-hydroxyl group induced sequential Michael-lactonization reactions on 2-(2-nitrovinyl)phenols with alkyl cyclopentanone-2-carboxylates in the presence of a catalytic amount of quinine-NH-thiourea followed by p-TSA.

AB - A general approach to asymmetric synthesis of highly substituted spirodihydrocoumarins with a quaternary stereocenter was achieved through neighboring ortho-hydroxyl group induced sequential Michael-lactonization reactions on 2-(2-nitrovinyl)phenols with alkyl cyclopentanone-2-carboxylates in the presence of a catalytic amount of quinine-NH-thiourea followed by p-TSA.

UR - http://www.scopus.com/inward/record.url?scp=84862547343&partnerID=8YFLogxK

U2 - 10.1039/c2ob07122c

DO - 10.1039/c2ob07122c

M3 - Article (Academic Journal)

C2 - 22391626

AN - SCOPUS:84862547343

SN - 1477-0520

VL - 10

SP - 5825

EP - 5829

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 30

ER -

Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: Synthesis of highly substituted chiral spirodihydrocoumarins

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