Stereoselectivity in Trimethylenemethane (TMM) Diyl Mediated Cycloaddition Reaction to Angularly Fused Triquinanes

Title
Stereoselectivity in Trimethylenemethane (TMM) Diyl Mediated Cycloaddition Reaction to Angularly Fused Triquinanes
Authors
강택윤여권이희윤
Keywords
carbenes; cycloaddition; stereoselectivity; trimethylenemethane; triquinane
Issue Date
2011-02
Publisher
Chemistry, an Asian journal
Citation
VOL 6, NO 2-651
Abstract
A thorough study on the diastereoselectivity in the TMM diyl mediated [2+3] cycloaddition reaction of monosubstituted linear substrates to form angularly fused triquinanes was carried out. Substitution at position 3 provided complete diastereoselectivity, while positions 1 and 4 induced marginal stereoselectivity. Position 2 did not show any influence on the diastereoselectivity. Position 4 turned out to be incompatible with the cycloaddition reaction as the carbene intermediate underwent O-Si bond insertion to form a dihydrofuran ring.
URI
http://pubs.kist.re.kr/handle/201004/67144
ISSN
1861-4728
Appears in Collections:
KIST Publication > Article
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