Journal of Organic Chemistry p. 1536 - 1539 (1987)
Update date:2022-08-04
Topics:
Elsevier, Cornelis J.
Mooiweer, Hendrik H.
The absolute configuration of (+)-t-Bu(Me)C(OH)C<*>CH ((+)-2a) has been reassigned S.This is shown by chemical correlation to its constitutional isomer (S)-t-Bu(H)C(OH)C<*>CMe, applying organocopper (I) reactions of known anti stereochemistry.Reaction of LiCuX2 with esters of (+)-2a gives (-)-t-Bu(Me)C=C=C(H)X (X = Cl, 1a; X = Br, 1b).The R configuration is attributed to these levorotatory halogenoallenes, on the basis of the known anti stereochemistry of the 1,3-substitution and the S configuration of (+)-2a.These new assignments lift a considerable confusion in the literature concerning absolute configuration of 1a and 2a.Implications regarding (semi)empirical rules, relating the sign of the optical rotation of a chiral allene to its configuration, are discussed.
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