Synthesis of Sterically-Crowded Olefins, gem-Dihaloalkenes, Butatrienes, and Thioketenes through the Reaction of Substituted Bornane-2-thiones or Bornane-2-selones with Conventional Carbenes or Metal Carbenoids-Reference-Cited by-同舟云学术

Synthesis of Sterically-Crowded Olefins, gem-Dihaloalkenes, Butatrienes, and Thioketenes through the Reaction of Substituted Bornane-2-thiones or Bornane-2-selones with Conventional Carbenes or Metal Carbenoids

Published:2013-07 Issue:7 Volume:8 Page:1934578X1300800
ISSN:1934-578X
Container-title:Natural Product Communications
language:en
Short-container-title:Natural Product Communications

Author:

Shimada Kazuaki¹,Sasaki Jun¹,Kishi Anna¹,Aoyagi Shigenobu¹,Takikawa Yuji¹

Affiliation:

1. Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University, Morioka, Iwate 020-8551, Japan

Abstract

Reaction of highly-substituted bornane-2-selones with a diazoalkane in the presence of either Rh2(OAc)4 or CuCl formed sterically-crowded exo-methylenic products, and similar treatment of the thiones or selones with dihalocarbenes or a propadienylidene carbene also formed dihaloalkenes, butatrienes, and thioketenes. All these reactions were assumed to proceed through a pathway involving the in situ formation and subsequent ring closure of chalcogenocarbonyl ylides.

Publisher

SAGE Publications

Subject

Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine

Link

http://journals.sagepub.com/doi/pdf/10.1177/1934578X1300800702

Reference74 articles.

1. Toward the Development of a General Chiral Auxiliary. A Total Synthesis of (+)-Tetronolide via a Tandem Ketene-Trapping [4 + 2] Cycloaddition Strategy

2. Catalytic Michael Reactions of Ketoesters with a Camphor-Derived Acrylate Equivalent: Stereoselective Access to All-Carbon Quaternary Centers

3. Synthesis of α-Amino Acids Based on Chiral Tricycloiminolactone Derived from Natural (+)-Camphor

4. Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes

5. Camphor-annelated imidazolines with various N1 and C2 pendants as tunable ligands for nitroaldol reactions