TY - JOUR
T1 - Syntheses of chiral lactones via asymmetric allylboration
AU - Reddy, M. Venkat Ram
AU - Brown, Herbert C.
AU - Ramachandran, P. Veeraraghavan
PY - 2001
Y1 - 2001
N2 - The syntheses of lactenones and lactones of different ring sizes in high enantiomeric excesses involving asymmetric allylboration with B-allyldiisopinocampheylborane have been described (1). γ-Substituted γ-butyolactones have been synthesized from homoallyl alcohols via a protection-hydroboration-oxidation-deprotection-cyclization sequence. The unique nature of α-perfluoroalkyl homoallyl alcohols has been exploited for the synthesis of γ-perfluoroalkyl γ-butyrolactones without protecting the alcohols. Allylboration of formyl esters provide a general route to prepare ω-allyl and ω-propyllactones. The ring-closing metathesis of homoallyl enoates provides a methodology to prepare a variety of α-pyranone-containing natural products.
AB - The syntheses of lactenones and lactones of different ring sizes in high enantiomeric excesses involving asymmetric allylboration with B-allyldiisopinocampheylborane have been described (1). γ-Substituted γ-butyolactones have been synthesized from homoallyl alcohols via a protection-hydroboration-oxidation-deprotection-cyclization sequence. The unique nature of α-perfluoroalkyl homoallyl alcohols has been exploited for the synthesis of γ-perfluoroalkyl γ-butyrolactones without protecting the alcohols. Allylboration of formyl esters provide a general route to prepare ω-allyl and ω-propyllactones. The ring-closing metathesis of homoallyl enoates provides a methodology to prepare a variety of α-pyranone-containing natural products.
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U2 - 10.1021/bk-2001-0783.ch016
DO - 10.1021/bk-2001-0783.ch016
M3 - Article
AN - SCOPUS:0041848638
VL - 783
SP - 220
EP - 234
JO - ACS Symposium Series
JF - ACS Symposium Series
SN - 0097-6156
ER -