A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon

Fengrui Lang; Daniel Zewge; Zhiguo J. Song; Mirlinda Biba; Peter Dormer; David Tschaen; R. P. Volante; Paul J. Reider

doi:10.1016/S0040-4039(03)01220-6

A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon

Fengrui Lang
, Daniel Zewge
, Zhiguo J. Song
, Mirlinda Biba
, Peter Dormer
, David Tschaen
, R. P. Volante
, Paul J. Reider

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

12 Scopus citations

Abstract

A highly stereoselective aldol reaction was observed on chromane carboxylate ester 1 via the corresponding diisopinocampheyl boron-enolate using commercially available (-)-DIP-Cl reagent. The aldol product 2c was obtained in 89% yield with 48 dr and 92% ee. Further studies indicate that stereoselective formation of the enolate and proper chiral ligand on boron are responsible for the exceptional diastereo- and enantioselectivity in the aldol reaction.

Original language	English (US)
Pages (from-to)	5285-5288
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	28
DOIs	https://doi.org/10.1016/S0040-4039(03)01220-6
State	Published - Jul 7 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(03)01220-6

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title = "A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon",

abstract = "A highly stereoselective aldol reaction was observed on chromane carboxylate ester 1 via the corresponding diisopinocampheyl boron-enolate using commercially available (-)-DIP-Cl reagent. The aldol product 2c was obtained in 89\% yield with 48 dr and 92\% ee. Further studies indicate that stereoselective formation of the enolate and proper chiral ligand on boron are responsible for the exceptional diastereo- and enantioselectivity in the aldol reaction.",

author = "Fengrui Lang and Daniel Zewge and Song, \{Zhiguo J.\} and Mirlinda Biba and Peter Dormer and David Tschaen and Volante, \{R. P.\} and Reider, \{Paul J.\}",

year = "2003",

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day = "7",

doi = "10.1016/S0040-4039(03)01220-6",

language = "English (US)",

volume = "44",

pages = "5285--5288",

journal = "Tetrahedron Letters",

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T1 - A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon

AU - Lang, Fengrui

AU - Zewge, Daniel

AU - Song, Zhiguo J.

AU - Biba, Mirlinda

AU - Dormer, Peter

AU - Tschaen, David

AU - Volante, R. P.

AU - Reider, Paul J.

PY - 2003/7/7

Y1 - 2003/7/7

N2 - A highly stereoselective aldol reaction was observed on chromane carboxylate ester 1 via the corresponding diisopinocampheyl boron-enolate using commercially available (-)-DIP-Cl reagent. The aldol product 2c was obtained in 89% yield with 48 dr and 92% ee. Further studies indicate that stereoselective formation of the enolate and proper chiral ligand on boron are responsible for the exceptional diastereo- and enantioselectivity in the aldol reaction.

AB - A highly stereoselective aldol reaction was observed on chromane carboxylate ester 1 via the corresponding diisopinocampheyl boron-enolate using commercially available (-)-DIP-Cl reagent. The aldol product 2c was obtained in 89% yield with 48 dr and 92% ee. Further studies indicate that stereoselective formation of the enolate and proper chiral ligand on boron are responsible for the exceptional diastereo- and enantioselectivity in the aldol reaction.

UR - https://www.scopus.com/pages/publications/0038684476

UR - https://www.scopus.com/pages/publications/0038684476#tab=citedBy

U2 - 10.1016/S0040-4039(03)01220-6

DO - 10.1016/S0040-4039(03)01220-6

M3 - Article

AN - SCOPUS:0038684476

SN - 0040-4039

VL - 44

SP - 5285

EP - 5288

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 28

ER -

A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon

Abstract

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