Hodgson, David M. Chung, Ying Kit Nuzzo, Irene Freixas, Glòria Kulikiewicz, Krystyna K. Cleator, Ed Paris, Jean-Marc Intramolecular Cyclopropanation of Unsaturated Terminal Epoxides and Chlorohydrins Lithium 2,2,6,6-tetramethylpiperidide (LTMP)-induced intramolecular cyclopropanation of unsaturated terminal epoxides provides an efficient and completely stereoselective entry to bicyclo[3.1.0]hexan-2-ols and bicyclo[4.1.0]heptan-2-ols. Further elaboration of C-5 and C-6 stannyl-substituted bicyclo[3.1.0]hexan-2-ols via Sn−Li exchange/electrophile trapping or Stille coupling generates a range of substituted bicyclic cyclopropanes. An alternative straightforward cyclopropanation protocol using a catalytic amount of 2,2,6,6-tetramethylpiperidine (TMP) allows for a convenient (1 g−7.5 kg) synthesis of bicyclo[3.1.0]hexan-2-ol and other bicyclic adducts. The synthetic utility of this chemistry has been demonstrated in a concise asymmetric synthesis of (+)-β-cuparenone. The related unsaturated chlorohydrins also undergo intramolecular cyclopropanation via in situ epoxide formation. TMP;LTMP;bicyclo;Unsaturated Terminal Epoxides;intramolecular cyclopropanation;terminal epoxides;epoxide formation;synthesis;cyclopropanation protocol;Intramolecular Cyclopropanation;bicyclic adducts;bicyclic cyclopropanes;stereoselective entry 2007-04-11
    https://acs.figshare.com/articles/journal_contribution/Intramolecular_Cyclopropanation_of_Unsaturated_Terminal_Epoxides_and_Chlorohydrins/3013546
10.1021/ja0672932.s001