Diastereoselective addition of methylmetal reagents to 2-methylaldehydes.

• The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-butyl moiety of high diastereomeric purity is described. These compounds can serve as potential building blocks for the preparation of several kinds of natural products. The diastereoselective addition of a number of methylmetal derivatives to three 3-substituted 2-methylaldehydes in various solvents was studied. An excellent diastereomeric. ratio (95:5 anti-Cram/Crain) was obtained with 2-methyl-3-(phenylsulfanyl)propanal (5) and Me2Zn in the presence of TiCl4.

Ämnesord

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Nyckelord

addition

asymmetric induction

diastereoselection

chelation

Organic chemistry

Organisk kemi

Chemistry

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