trans-hydroalumination/alkylation: one-pot synthesis of trisubstituted allylic alcohols.
[reaction: see text] Described herein is a method of stereoselective synthesis of trisubstituted allylic alcohols by alkylation of alkenyl alanates, formed in situ through treatment of propargyl alcohols with Vitride (Red-Al). This technique represents the first of its kind to feature a trans-hydrometalation, and is particularly effective for the formation of 1,4-dienes. Applications involving primary, secondary, and tertiary alcohols are discussed, as well as limitations regarding both alkyne and electrophile components.
Langille
Neil F
NF
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Jamison
Timothy F
TF
D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D000535:Aluminum / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D020005:Propanols; C006463:allyl alcohol; D000535:Aluminum; C028255:propargyl alcohol; D000409:Alanine