期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 8, 页码 3925-3931出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja300472a
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资金
- National Institutes of Health [GM038436]
The stereocontrolled synthesis of the beta-branched anti,anti-dipropionate stereotriad 4 via aldol or crotylmetal chemistry represents a historical challenge to the organic synthesis community. Here we describe a general solution to the long-standing problem associated with the synthesis of 4 by utilizing mismatched double asymmetric crotylboration reactions of enantioenriched alpha-methyl substituted aldehydes with the chiral, nonracemic crotylborane reagent (S)-(E)-22 (or its enantiomer). This method not only provides direct access to anti,anti-dipropionate stereotriads 24 [a synthetic equivalent of 4] with very good (5-8:1) if not excellent (>= 15:1) diastereoselectivity from beta-branched chiral aldehydes with <= 50:1 intrinsic diastereofacial selectivity preferences but also provides a vinylstannane unit in the products that is properly functionalized for use in subsequent C-C bond-forming events. We anticipate that this method will be widely applicable and will lead to substantial simplification of strategies for synthesis of polyketide natural products.
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