Skip to main page content
Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
, 10 (22), 5313-6

Siloxacyclopentenes as Dienophile-Linked Directing Groups in Intramolecular Diels-Alder Reactions

Affiliations

Siloxacyclopentenes as Dienophile-Linked Directing Groups in Intramolecular Diels-Alder Reactions

Geoff T Halvorsen et al. Org Lett.

Abstract

The synthesis and intramolecular Diels-Alder reactions of trienes 5 and 6 with a siloxacyclopentene-constrained dienophile are described. These reactions provide the primary cycloadducts 7 and 8 with high diastereoselectivity. These cycloadducts possess trans-relationships between the ring fusion proton and the adjacent C(1) alkoxy group and can be further elaborated to alcohols 9 and 11 (via protiodesilylation) or to 10 and 12 (via Fleming-Tamao oxidation) depending on the substitutent R.

Figures

Scheme 1
Scheme 1
Stereochemical Directing Group Strategies for IMDA Reactions
Scheme 2
Scheme 2
Strategy for Intramolecular Diels-Alder Cyclizations of Siloxacyclopentene-Constrained Trienes 5 and 6
Scheme 3
Scheme 3
Synthesis of Nonatrienes 5a-c
Scheme 4
Scheme 4
Synthesis of Decatrienes 6a-c
Scheme 5
Scheme 5
Attempted Hydrosilylation of 19d

Similar articles

See all similar articles

Cited by 2 PubMed Central articles

Publication types

Feedback