Chemo- and Diastereoselective Michael-Michael-Acetalization Cascade for the Synthesis of 1,3-Indandione-Fused Spiro[4.5]decan Scaffolds

Shu Mei Yang; Yi Ling Tsai; Ganapuram Madhusudhan Reddy; Lennart Möhlmann; Wenwei Lin

doi:10.1021/acs.joc.7b01415

Chemo- and Diastereoselective Michael-Michael-Acetalization Cascade for the Synthesis of 1,3-Indandione-Fused Spiro[4.5]decan Scaffolds

Shu Mei Yang
, Yi Ling Tsai
, Ganapuram Madhusudhan Reddy
, Lennart Möhlmann
, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

27 Citations (Scopus)

Abstract

A novel, organobase-catalyzed and highly chemoselective Michael-Michael-acetalization cascade is presented for the efficient synthesis of spiro-indandione skeletons. Following this very simple protocol, a broad range of products was obtained in good yields with excellent diastereocontrol. The role of steric factors in the acetalization step was evaluated.

Original language	English
Pages (from-to)	9182-9190
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	82
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.7b01415
Publication status	Published - 2017 Sept 1

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.7b01415

Cite this

@article{55eb67c2e3fa48218f856442f5a697fc,

title = "Chemo- and Diastereoselective Michael-Michael-Acetalization Cascade for the Synthesis of 1,3-Indandione-Fused Spiro[4.5]decan Scaffolds",

abstract = "A novel, organobase-catalyzed and highly chemoselective Michael-Michael-acetalization cascade is presented for the efficient synthesis of spiro-indandione skeletons. Following this very simple protocol, a broad range of products was obtained in good yields with excellent diastereocontrol. The role of steric factors in the acetalization step was evaluated.",

author = "Yang, \{Shu Mei\} and Tsai, \{Yi Ling\} and Reddy, \{Ganapuram Madhusudhan\} and Lennart M{\"o}hlmann and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = sep,

day = "1",

doi = "10.1021/acs.joc.7b01415",

language = "English",

volume = "82",

pages = "9182--9190",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Chemo- and Diastereoselective Michael-Michael-Acetalization Cascade for the Synthesis of 1,3-Indandione-Fused Spiro[4.5]decan Scaffolds

AU - Yang, Shu Mei

AU - Tsai, Yi Ling

AU - Reddy, Ganapuram Madhusudhan

AU - Möhlmann, Lennart

AU - Lin, Wenwei

PY - 2017/9/1

Y1 - 2017/9/1

N2 - A novel, organobase-catalyzed and highly chemoselective Michael-Michael-acetalization cascade is presented for the efficient synthesis of spiro-indandione skeletons. Following this very simple protocol, a broad range of products was obtained in good yields with excellent diastereocontrol. The role of steric factors in the acetalization step was evaluated.

AB - A novel, organobase-catalyzed and highly chemoselective Michael-Michael-acetalization cascade is presented for the efficient synthesis of spiro-indandione skeletons. Following this very simple protocol, a broad range of products was obtained in good yields with excellent diastereocontrol. The role of steric factors in the acetalization step was evaluated.

UR - https://www.scopus.com/pages/publications/85028741766

UR - https://www.scopus.com/pages/publications/85028741766#tab=citedBy

U2 - 10.1021/acs.joc.7b01415

DO - 10.1021/acs.joc.7b01415

M3 - Article

C2 - 28759248

AN - SCOPUS:85028741766

SN - 0022-3263

VL - 82

SP - 9182

EP - 9190

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Chemo- and Diastereoselective Michael-Michael-Acetalization Cascade for the Synthesis of 1,3-Indandione-Fused Spiro[4.5]decan Scaffolds

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 1472949: Experimental Crystal Structure Determination

CCDC 1400556: Experimental Crystal Structure Determination

CCDC 1472948: Experimental Crystal Structure Determination

Cite this

Chemo- and Diastereoselective Michael-Michael-Acetalization Cascade for the Synthesis of 1,3-Indandione-Fused Spiro[4.5]decan Scaffolds

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1472949: Experimental Crystal Structure Determination

CCDC 1400556: Experimental Crystal Structure Determination

CCDC 1472948: Experimental Crystal Structure Determination

Cite this