Intramolecular S(N)2' cyclization of an alkyllithium species onto a methoxy allyl ether is syn selective.
The preference for syn- or anti-addition of an intramolecular S(N)2[prime or minute] cyclization of an alkyllithium species onto a methoxy allyl ether has been proven unequivocally to take place by a syn S(N)2[prime or minute] mechanism.
La Cruz
Thomas E
TE
Department of Chemistry, 516 Rowland Hall, University of California Irvine, Irvine, California 92697-2025, USA. srychnov@uci.edu
Rychnovsky
Scott D
SD
D000498:Allyl Compounds / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D003500:Cyclization; D004988:Ethers, Cyclic / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000498:Allyl Compounds; D000577:Amides; D004988:Ethers, Cyclic; D009942:Organometallic Compounds; D008094:Lithium; D000432:Methanol