4_20_05 - Tables removed due to copyright reasons....

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Massachusetts Institute of Technology Organic Chemistry 5.512 April 20, 2005 Prof. Rick L. Danheiser Crotylmetal Additions to α -Chiral Aldehydes R CHO R OH 4 5 3 Substrate Control: Addition of Achiral Allylmetals to α− Chiral Aldehydes Reagent Control: Addition of Chiral Allylmetals to Achiral Aldehydes Reagent Control: Addition of Allylmetals to Achiral Aldehydes (w/ Chiral Lewis Acids) Addition of Chiral Allylmetals to α− Chiral Aldehydes Crotylmetal Additions: 3,4-Stereochemistry (Intrinsic Diastereoselection) Crotymetal Additions to α− Chiral Aldehydes Crotylation with Leighton Reagents Hackman, B. M.; Lombardi, P. J.; Leighton, J. L. Org. Lett. 2004 , 6 , 4375
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Unformatted text preview: Tables removed due to copyright reasons. Construction of Stereotriads R R 4 5 3 CHO OH Retron C-4/C-5 C-3/C-4 C-3/C-5 Best Reagent Felkin Anti No Gauche Pentane B O R OH O R R R OH OH OH BIpc 2 Gauche Anti-Felkin Anti Pentane TiCp(TADDOL) BIpc 2 Anti-Felkin Syn No Gauche Pentane CO 2 i-Pr O B O CO 2-Pr Gauche SnBu 3 Felkin Syn Pentane + BF 3-Et 2 O Case Study: Addition of Crotylmetal Compounds to Aldehydes OH O H 3 C H 3 C CH 3 CH 3 CH 3 CH 3 O O O O 3 N O H O 3 3 3 3 O H H l. J m em oc. , OMe OH OAc OH CH OMe CH OR CH OAc CH CH OR W. R. Roush et a . A . Ch . S 1990 112 , 6348 27 26 25 24 23 22 21 20 27 26 25 24 23 22 21 20 Figures removed due to copyright reasons....
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This note was uploaded on 11/27/2011 for the course CHEM 5.43 taught by Professor Timothyf.jamison during the Spring '07 term at MIT.

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4_20_05 - Tables removed due to copyright reasons....

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