On February 21, 2009, Davies, Stephen G.; Durbin, Matthew J.; Goddard, Euan C.; Kelly, Peter M.; Kurosawa, Wataru; Lee, James A.; Nicholson, Rebecca L.; Price, Paul D.; Roberts, Paul M.; Russell, Angela J.; Scott, Philip M.; Smith, Andrew D. published an article.Reference of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole The title of the article was Doubly diastereoselective conjugate addition of homochiral lithium amides to homochiral α,β-unsaturated esters containing cis- and trans-dioxolane units. And the article contained the following:
As part of a long-term goal directed towards the ab initio asym. synthesis of unnatural amino sugars, the doubly diastereoselective conjugate addition reactions of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of homochiral α,β-unsaturated esters containing cis- and trans-dioxolane units was investigated. These reactions resulted in “matching” and “mismatching” effects. In the “matched” cases a single diastereoisomer of the corresponding β-amino ester (containing three contiguous stereocentres) is produced. Upon conjugate addition to a homochiral α,β-unsaturated ester containing a cis-dioxolane unit, in the “mismatched” case it is the stereocontrol of the substrate which is dominant over that of the lithium amide, while upon addition to homochiral α,β-unsaturated esters containing a trans-dioxolane unit the stereocontrol of the homochiral lithium amide is dominant. Hydrogenolytic N-deprotection of the β-amino ester products of conjugate addition gives access to polyoxygenated β-amino acid derivatives The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Reference of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
The Article related to amino acid beta polyoxygenated asym synthesis chirality crystal structure, dioxolane unsaturated ester diastereoselective conjugate addition lithium amide hydrogenolysis, hydrogenolysis reductive amination solvent effect, crystal structure beta amino acid benzyl methylbenzylamino isopropylidene heptanoate and other aspects.Reference of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem