Organic Chemistry

Lecture Outline

Prochirality

PROCHIRALITY
Prochiral molecules are those that can be converted from a achiral molecule to a chiral
molecule in a single step.
Prochirality may be the result of an sp2 carbon being converted to a chiral sp3 carbon via a
reaction (see Nu acyl addition below) or by substitution of a “prochiral” substituent (usually
hydrogen) with another substituent that results in a chiral center.

PRO-R and PRO-S SUBSTITUENTS
OH
Ha

Hb

substitute Ha with CH3

substitute Hb with CH3

OH
H3C

OH
Ha

Hb

CH3

R-configuration

S-configuration

Ha is referred to as "pro-R"

Hb is referred to as "pro-S"

PROCHIRALITY IN NUCLEOPHILIC ACYL ADDITIONS
Prochiral carbonyl carbons are carbons that when reacted with a nucleophile result in the
formation of a new chiral center.
Nu:

Nu

Nu

R'

R'

R'
O

O

R

R

OH

O

R'

OH

R

O
R

Nu:

R'

R'
R

Nu

R

Nu

front face is called the Re face and the back face is referred to as the Si face. assign Re and Si faces Nucleophiles may attack carbonyl groups from the Re face or the Si face. The stereochemistry of the product depends on the priorities of the substituents and the priority of the nucleophile. The two sides of the carbonyl group (front and back) are referred to as "faces".Organic Chemistry Lecture Outline Prochirality The carbonyl group has a trigonal planar geometry (sp2). Front Back O "Si face" R O R' R R' "Re face" orientation of substituents is counterclockwise "Si face" 1 1 O 3 2 O flip over to put in the proper orientation 2 3 "Re face" once it is in the proper orientation. When the priorities of three substituents of the carbonyl group are oriented in a clockwise fashion (highest --> lowest). .

H+ Stereochemistry of the new chiral center is S Nu reacts on the Re face 1 O OH 2 1.Organic Chemistry Lecture Outline Prochirality 1 O 1. NaBH4 3 H3C H3C H 2. 2 OH MgBr H3C 3 H3C 2. H+ H Nu reacts on the Re face Stereochemistry of the new chiral center is R .