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Volumn 70, Issue 2, 2005, Pages 590-595

The rearrangement route to 3-carboxy- and 3-hydroxymethyl-2-azabicyclo[2.1. 1]hexanes: 3,5-Methanoprolines

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 12344283549     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0484171     Document Type: Article
Times cited : (21)

References (57)
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    • note
    • The rearrangement of alcohol 22 might be envisioned as occurring through a series of steps shown in Scheme 5. An alcohol proton catalyzed ring opening could give a β-silyl cation i. A subsequent 1,2-alkyl shift gives a ring-enlarged cation ii. Proton loss generates an allylic silane iii. Desilylation accompanied by bromide elimination gives diene iv and a series of acid-catalyzed proton transfers affords ketone 23.


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