High 1,6 diastereoselectivity in the hydride reduction of an acyclic ketone substrate via bicyclic chelation control

DOI: 10.1016/0040-4039(96)01767-4

Source and publish data:

Tetrahedron Letters p. 7897 - 7900 (1996)

Update date:2022-08-03

Topics:

Authors:

Zhang, Han-Cheng

Harris, Bruce D.

Maryanoff, Cynthia A.

Maryanoff, Bruce E.

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Article abstract of DOI:10.1016/0040-4039(96)01767-4

Reduction of acyclic ε-hydroxy ketone 3 with R-Alpine-Hydride in methylene chloride provided a strong preponderance of the anti diasteromer of 4 (anti:syn = 12:1). This impressive 1,6 stereoselectivity is attributed to bicyclic chelation control of hydride addition.

Full text of DOI:10.1016/0040-4039(96)01767-4

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