Abstract
Enantiomerically enriched bicyclo[m.1.0]alkan-2-ones having larger ring sizes between five and 16 members were prepared and subjected to additions of nucleophiles to the carbonyl carbon. Such additions were efficient and highly diastereoselective for all nucleophiles for bicycles with ring sizes greater than seven. Diastereoselectivity for these additions is rationalized by assuming early transition states and exposure of the same carbonyl face to the ring exterior in the vast majority of populated conformers for each bicyclic ketone.
Original language | English (US) |
---|---|
Pages (from-to) | 2743-2752 |
Number of pages | 10 |
Journal | Journal of Organic Chemistry |
Volume | 61 |
Issue number | 8 |
DOIs | |
State | Published - Apr 19 1996 |
ASJC Scopus subject areas
- Organic Chemistry
Fingerprint
Dive into the research topics of 'Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 2. Nucleophilic additions to the carbonyl carbons of bicyclot[m.1.0]alkan-2-ones'. Together they form a unique fingerprint.Datasets
-
CCDC 125283: Experimental Crystal Structure Determination
Mash, E. A. (Contributor), Gregg, T. M. (Creator) & Kaczynski, M. A. (Creator), Cambridge Crystallographic Data Centre, 1996
DOI: 10.5517/cc46cd2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc46cd2&sid=DataCite
Dataset
-
CCDC 125282: Experimental Crystal Structure Determination
Mash, E. A. (Contributor), Gregg, T. M. (Creator) & Kaczynski, M. A. (Creator), Cambridge Crystallographic Data Centre, 1996
DOI: 10.5517/cc46cc1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc46cc1&sid=DataCite
Dataset